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MODERN GREEN CHEMISTRY AND
HETEROCYCLIC COMPOUNDS
Molecular Design, Synthesis, and
Biological Evaluation
 Innovations in Physical Chemistry: Monograph Series

MODERN GREEN CHEMISTRY AND

HETEROCYCLIC COMPOUNDS
Molecular Design, Synthesis, and
Biological Evaluation

Edited by
Ravindra S. Shinde, PhD
A. K. Haghi, PhD
Apple Academic Press Inc. Apple Academic Press, Inc.
4164 Lakeshore Road 1265 Goldenrod Circle NE
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© 2020 by Apple Academic Press, Inc.
Exclusive worldwide distribution by CRC Press, a member of Taylor & Francis Group
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This book contains information obtained from authentic and highly regarded sources. Reprinted material
is quoted with permission and sources are indicated. Copyright for individual articles remains with the
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Library and Archives Canada Cataloguing in Publication
Title: Modern green chemistry and heterocyclic compounds : molecular design, synthesis, and
biological evaluation / edited by Ravindra S. Shinde, PhD, A.K. Haghi, PhD.
Names: Shinde, Ravindra S., 1979- editor. | Haghi, A. K., editor.
Series: Innovations in physical chemistry.
Description: Series statement: Innovations in physical chemistry: monographic series | Includes
bibliographical references and index.
Identifiers: Canadiana (print) 20200176994 | Canadiana (ebook) 2020017701X |
ISBN 9781771888325 (hardcover) | ISBN 9780429328602 (ebook)
Subjects: LCSH: Heterocyclic compounds. | LCSH: Green chemistry.
Classification: LCC QD400 .M63 2020 | DDC 547/.59—dc23

CIP data on file with US Library of Congress

Apple Academic Press also publishes its books in a variety of electronic formats. Some content that
appears in print may not be available in electronic format. For information about Apple Academic
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ABOUT THE EDITORS

Ravindra S. Shinde, PhD

Assistant Professor, Department of Chemistry and Industrial Chemistry,
Dayanand Science College, Latur, Maharashtra, India
Ravindra S. Shinde, PhD, is presently serving as Assistant Professor in the
Department of Chemistry and Industrial Chemistry at Dayanand Science
College, Latur, in Maharashtra, India. He is reviewer of many national
and international of journals, including Medicinal Chemistry Research,
the United Journal of Chemistry, and the Journal of Emerging Technology
and Innovation Research, and is also an Advisory Board Member of the
European Journal of Biomedical and Pharmaceutical Sciences. He has
published many research papers in reputed national and international jour-
nals. He has completed his BSc, MSc, BEd, and PhD degrees from Swami
Ramanand Teerth Marathwada University, Nanded, India.

A. K. Haghi, PhD
Professor Emeritus of Engineering Sciences, Editor-in-Chief,
International Journal of Chemoinformatics and Chemical Engineering &
Polymers Research Journal; Member, Canadian Research and
Development Center of Sciences and Cultures (CRDCSC), Canada
A. K. Haghi, PhD, is the author and editor of 165 books, as well as 1000
published papers in various journals and conference proceedings. Dr. Haghi
has received several grants, consulted for a number of major corporations,
and is a frequent speaker to national and international audiences. Since
1983, he served as professor at several universities. He is the former Editor-
in-Chief of the International Journal of Chemoinformatics and Chemical
Engineering and Polymers Research Journal and is on the editorial boards
of many international journals. He is also a member of the Canadian
Research and Development Center of Sciences and Cultures (CRDCSC),
Montreal, Quebec, Canada. He holds a BSc in urban and environmental
vi About the Editors

engineering from the University of North Carolina (USA), an MSc in

mechanical engineering from North Carolina A&T State University (USA),
a DEA in applied mechanics, acoustics and materials from the Université
de Technologie de Compiègne (France), and a PhD in engineering sciences
from Université de Franche-Comté (France).
INNOVATIONS IN PHYSICAL
CHEMISTRY: MONOGRAPH SERIES

This book series offers a comprehensive collection of books on phys-

ical principles and mathematical techniques for majors, non-majors,
and chemical engineers. Because there are many exciting new areas of
research involving computational chemistry, nanomaterials, smart mate-
rials, high-performance materials, and applications of the recently discov-
ered graphene, there can be no doubt that physical chemistry is a vitally
important field. Physical chemistry is considered a daunting branch of
chemistry—it is grounded in physics and mathematics and draws on
quantum mechanics, thermodynamics, and statistical thermodynamics.
Editors-in-Chief
A. K. Haghi, PhD
Former Editor-in-Chief, International Journal of Chemoinformatics
and Chemical Engineering and Polymers Research Journal; Member,
Canadian Research and Development Center of Sciences and Cultures
(CRDCSC), Montreal, Quebec, Canada
E-mail: [email protected]

Lionello Pogliani, PhD

University of Valencia-Burjassot, Spain
E-mail: [email protected]

Ana Cristina Faria Ribeiro, PhD

Researcher, Department of Chemistry, University of Coimbra, Portugal
E-mail: [email protected]

BOOKS IN THE SERIES

• Applied Physical Chemistry with Multidisciplinary Approaches
Editors: A. K. Haghi, PhD, Devrim Balköse, PhD, and
Sabu Thomas, PhD
• Biochemistry, Biophysics, and Molecular Chemistry: Applied
Research and Interactions
Editors: Francisco Torrens, PhD, Debarshi Kar Mahapatra, PhD, and
A. K. Haghi, PhD
viii Innovations in Physical Chemistry: Monograph Series

• Chemistry and Industrial Techniques for Chemical Engineers

Editors: Lionello Pogliani, PhD, Suresh C. Ameta, PhD, and
A. K. Haghi, PhD
• Chemistry and Chemical Engineering for Sustainable
Development: Best Practices and Research Directions
Editors: Miguel A. Esteso, PhD, Ana Cristina Faria Ribeiro, and
A. K. Haghi, PhD
• Chemical Technology and Informatics in Chemistry with
Applications
Editors: Alexander V. Vakhrushev, DSc, Omari V. Mukbaniani, DSc,
and Heru Susanto, PhD
• Engineering Technologies for Renewable and Recyclable
Materials: Physical-Chemical Properties and Functional Aspects
Editors: Jithin Joy, Maciej Jaroszewski, PhD, Praveen K. M.,
and Sabu Thomas, PhD, and Reza Haghi, PhD
• Engineering Technology and Industrial Chemistry with
Applications
Editors: Reza Haghi, PhD, and Francisco Torrens, PhD
• High-Performance Materials and Engineered Chemistry
Editors: Francisco Torrens, PhD, Devrim Balköse, PhD,
and Sabu Thomas, PhD
• Methodologies and Applications for Analytical and Physical
Chemistry
Editors: A. K. Haghi, PhD, Sabu Thomas, PhD, Sukanchan Palit,
and Priyanka Main
• Modern Physical Chemistry: Engineering Models, Materials,
and Methods with Applications
Editors: Reza Haghi, PhD, Emili Besalú, PhD,
Maciej Jaroszewski, PhD, Sabu Thomas, PhD, and Praveen K. M.
• Molecular Chemistry and Biomolecular Engineering: Integrating
Theory and Research with Practice
• Editors: Lionello Pogliani, PhD, Francisco Torrens, PhD, and
A. K. Haghi, PhD
• Modern Green Chemistry and Heterocyclic Compounds:
Molecular Design, Synthesis, and Biological Evaluation
Editors: Ravindra S. Shinde, and A. K. Haghi, PhD
Innovations in Physical Chemistry: Monograph Series ix

• Physical Chemistry for Chemists and Chemical Engineers:

Multidisciplinary Research Perspectives
Editors: Alexander V. Vakhrushev, DSc, Reza Haghi, PhD,
and J. V. de Julián-Ortiz, PhD
• Physical Chemistry for Engineering and Applied Sciences:
Theoretical and Methodological Implication
Editors: A. K. Haghi, PhD, Cristóbal Noé Aguilar, PhD,
Sabu Thomas, PhD, and Praveen K. M.
• Practical Applications of Physical Chemistry in Food Science and
Technology
Editors: Cristóbal Noé Aguilar, PhD, Jose Sandoval Cortes, PhD,
Juan Alberto Ascacio Valdes, PhD, and A. K. Haghi, PhD
• Research Methodologies and Practical Applications of Chemistry
Editors: Lionello Pogliani, PhD, A. K. Haghi, PhD,
and Nazmul Islam, PhD
• Theoretical Models and Experimental Approaches in Physical
Chemistry: Research Methodology and Practical Methods
Editors: A. K. Haghi, PhD, Sabu Thomas, PhD, Praveen K. M.,
and Avinash R. Pai
• Theoretical and Empirical Analysis in Physical Chemistry:
A Framework for Research
Editors: Miguel A. Esteso, PhD, Ana Cristina Faria Ribeiro, PhD,
and A. K. Haghi, PhD
CONTENTS

Contributors ....................................................................................................... xiii

Abbreviations .......................................................................................................xv

Preface ............................................................................................................... xix

1. An Overview of the Organic Synthesis and Transformations

Initiated by Sulfate Radical Anions (SO4•–) Produced from
Aqueous Persulfate Solutions under Transition Metal-Free
Conditions .................................................................................................... 1
Priya and Palani Natarajan

2. Design and Synthesis of Triazine Amine Derivatives as

Antibacterial and Antifungal Agents....................................................... 59
Ravindra S. Shinde and Shreyas S. Mahurkar

3. An Efficient Green Synthesis of Diphenyl Pyrazol-4-yl-Thio-

Pyridin-4-yl-1,3,4-Oxadiazole Derivatives and Evaluation of
Their Antimicrobial and Antioxidant Activity ....................................... 79
Ajay N. Ambhore

4. Multicomponent Synthesis of 2-Substituted Derivatives of

6-Amino-5-Cyano-1,4-Dihydro-3-Methyl-1,4-Diphenylpyrano-
[2,3-c]-Pyrazole Using Knoevenagel and Michael Addition................ 113
Jaman A. Angulwar

5. Triazole-Derived, Artesunate, and Metabolic Pathways for

Artemisinin .............................................................................................. 137
Francisco Torrens and Gloria Castellano

6. Facile Synthesis of Some 1,3,4 Thiadiazole-Based Ligands and

Their Metal Complexes as Potential Antimicrobial Agents ................ 145
Ajay M. Patil, Ravindra S. Shinde, and Sunil R. Mirgane

7. An Efficient and Green Synthesis of 2,3-Dihydroquinazolin-4

(1H)-One Derivatives Catalyzed by {[bmim]Methanesulfonate}
Ionic Liquid ............................................................................................. 159
Shreyas S. Mahurkar, Ravindra S. Shinde, and Sangita S. Makone
xii Contents

8. Synthesis, Characterization, and Biological Evaluation of

Substituted 2-Phenoxynicotinaldehydes as α-Amylase Inhibitor ....... 183
Kishan Prabhu Haval

9. Separation of Coffee Pulp Bioactive Phenolic Compounds by

MPLC Fractionation and Identification by HPLC-ESI-MS............... 217
Jorge E. Wong-Paz, Sylvain Guyot, Juan C. Contreras-Esquivel, Pedro Aguilar-Zárate,
Raúl Rodríguez-Herrera, and Cristóbal N. Aguilar

10. Trichoderma asperellum as Biological Control Agent:

Fungal Cellulase and Spore Production by
Solid-State Fermentation........................................................................ 229
Reynaldo De la Cruz-Quiroz, Sevastianos Roussos, Raúl Rodríguez-Herrera,
Daniel Hernandez-Castillo, and Cristóbal N. Aguilar

11. Knowledge Democratization and the Hidden Face of

Palm Oil Biodiesel ................................................................................... 239
Francisco Torrens and Gloria Castellano

12. Nanobiocomposites, Biomimetic Nanocomposites, and

Biologically Inspired Nanocomposites .................................................. 251
Shrikaant Kulkarni

Index ................................................................................................................. 289

CONTRIBUTORS

Cristóbal N. Aguilar
Bioprocesses and Bioproducts Group, Department of Food Research, School of Chemistry,
Autonomous University of Coahuila–25280, Saltillo, Coahuila, México,
E-mail: [email protected]

Pedro Aguilar-Zárate
Bioprocesses and Bioproducts Group, Department of Food Research, School of Chemistry,
Autonomous University of Coahuila–25280, Saltillo, Coahuila, México
Ajay N. Ambhore
Department of Chemistry, Padmabhushan Dr. Vasantraodada Patil College, Tasgaon,
Sangli (MS) India, E-mail: [email protected], [email protected]
Jaman A. Angulwar
Department of Chemistry, Dayanand Science College, Latur–413512, Maharashtra, India

Gloria Castellano
Department of Experimental Sciences and Mathematics, Faculty of Veterinary and Experimental
Sciences, Valencia Catholic University Saint Vincent Martyr, Guillem de Castro-94,
E-46001 Valencia, Spain

Juan C. Contreras-Esquivel
Bioprocesses and Bioproducts Group, Department of Food Research, School of Chemistry,
Autonomous University of Coahuila–25280, Saltillo, Coahuila, México

Reynaldo De la Cruz-Quiroz
Bioprocesses and Bioproducts Research Group, Food Research Department,
Autonomous University of Coahuila, 25280, Saltillo, México

Sylvain Guyot
INRA, UR1268 BIA, Team Polyphenol, Reactivity and Processing (PRP), BP–35327,
35653 Le Rheu, France

A. K. Haghi
Professor Emeritus of Engineering Sciences, Former Editor-in-Chief, International Journal of
Chemoinformatics and Chemical Engineering & Polymers Research Journal; Member,
Canadian Research and Development Center of Sciences and Cultures (CRDCSC), Canada
E-mail: [email protected]

Kishan Prabhu Haval

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Sub-Campus,
Osmanabad–413501, Maharashtra, India, E-mail: [email protected], [email protected]

Daniel Hernandez-Castillo
Agricultural Parasitology Department, Antonio Narro Agrarian Autonomous University,
Buenavista, Saltillo, Coahuila, México
xiv Contributors

Shrikaant Kulkarni
Assistant Professor, Vishwakarma Institute of Technology, Department of Chemical Engineering,
666, Upper Indira Nagar, Bibwewadi, Pune–411037, India, Mobile: +91-9970663353,
E-mail: [email protected]
Shreyas S. Mahurkar
Department of Chemistry, Dayanand Science College, Latur–413512, Maharashtra, India,
E-mail: [email protected], [email protected]
Sangita S. Makone
School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded–431606,
Maharashtra, India

Sunil R. Mirgane
Department of Chemistry, J.E.S. College, Jalna–431203 Maharashtra, India

Palani Natarajan
Assistant Professor, Department of Chemistry and Center for Advanced Studies in Chemistry,
Punjab University, Chandigarh–160014, U.T., India, E-mail: [email protected]
Ajay M. Patil
Department of Chemistry, Pratishthan Mahavidyalaya, Paithan–431107, Maharashtra, India,
E-mail: [email protected], [email protected]

Priya
Research Scholar, Department of Chemistry and Center for Advanced Studies in Chemistry,
Punjab University, Chandigarh–160014, U.T., India

Raúl Rodríguez-Herrera
Bioprocesses and Bioproducts Research Group, Department of Food Research,
School of Chemistry, Autonomous University of Coahuila–25280, Saltillo, Coahuila, México

Sevastianos Roussos
Mediterranean Institute of marine and terrestrial Biodiversity and Ecology, Marseille, France

Ravindra S. Shinde
Research Center in Chemistry, Dayanand Science College, Latur–413512, MS, India,
E-mail: [email protected]

Francisco Torrens
Institute for Molecular Science, University of Valencia, PO Box 22085, E-46071 Valencia, Spain,
E-mail: [email protected]

Jorge E. Wong-Paz
Bioprocesses and Bioproducts Group, Department of Food Research, School of Chemistry,
Autonomous University of Coahuila–25280, Saltillo, Coahuila, México
ABBREVIATIONS

C NMR
13
carbon nuclear magnetic resonance
H NMR
1
proton nuclear magnetic resonance
AA ascorbic acid
AAE aqueous acetone extract
AAs amino acids
Ac acetyl
AcOH acetic acid
AEs adverse effects
AIDS acquired immunodeficiency syndrome
Aq aqueous
Ar aryl
ART artemisinin
ARTDs ART derivatives
BC breast cancer
BCA biological control agents
BEC bleaching earth clay
But butyl
Cat catalyst
CC corn cob
CC cyanuric chloride
CDCl3 deuterated chloroform
CDMT 2-chloro-4,6-dimethoxy-1,3,5-triazine
CF coconut fiber
CLSI Clinical and Laboratory Standards Institute
CONACYT Coahuila and the National Council of Science and
Technology
Conc. concentrated
CVD chemical vapor deposition
D doublet
d doublet
DBSA dodecylbenzene sulfonic acid
Dd doublet of doublet
DHP dihydropyridines
xvi Abbreviations

DM diabetes mellitus
DMF N,N-dimethyl formamide
DMSO dimethyl sulfoxide
DNA deoxyribonucleic acid
DPPH diphenylpicrylhyride
EBX ethynylbenziodoxolone
EDA electron donor acceptor
EDTA ethylene diamine tetraacetic acid
ESI-MS infusion in electrospray mass spectrometry
Et ethyl
EtOAc ethylacetoacetate
EtOH ethanol
g gram
GHE greenhouse effect
HAT hydrogen atom transfer
HCl hydrochloric acid
hr hours
HTMAB hexadecyltrimethylammonium bromide
Hz hertz
IR infrared
K2CO3 potassium carbonate
KBr potassium bromide
Kg kilogram
M molar/multiplet
m multiplet
M.P. melting point
MASS mass-spectroscopy
MCRs multicomponent reactions
MDR multidrug resistance
Me methyl
MeOH methanol
mg milligram
MHz megahertz
MIC minimum inhibitory concentration
Min minute
ML methylene-lactone
mL milliliters
mm millimeter
Abbreviations xvii

mmol milimol
MPLC medium pressure liquid chromatography
Mtb mycobacterium tuberculosis
Na2CO3 sodium carbonate
NHS N-hydroxysuccinimide
nM nanometer
NMR nuclear magnetic resonance
NSCLC non-small cell lung cancer
OH hydroxy
PDA potato dextrose agar
PEG-400 poly ethylene glycol-400
Ph phenyl
PKC palm kernel cake
ppm parts per million
PTE periodic table of the elements
RCC radiochemical conversion
ROS reactive oxygen species
RT room temperature
S singlet
SAR structure-activity relationship
SCB sugarcane bagasse
SO4•− sulfate radical anions
SOR superoxide anion radical
SSF solid-state fermentation
STL sesquiterpene lactone
T triplet
t-But tert-Butyl
TEA triethylamine
TEAB tetraethyl ammonium bicarbonate
TEBA triethyl benzyl ammonium chloride
TEM transmission electron microscope
THR Trichoderma harzianum
TLC thin-layer chromatography
TMS tetramethylsilane
UAAAN Universidad Autónoma Agraria Antonio Narro
ZOI zone of inhibition
PREFACE

Green chemistry, or environmentally benign chemistry, is the design of

chemical products and processes that reduce or eliminate the use and
generation of hazardous substances.
Rather than focusing only on those undesirable substances that might
be inadvertently produced in a process, green chemistry also includes all
substances that are part of the process. Therefore, green chemistry is a tool
not only for minimizing the negative impact of those procedures aimed
at optimizing efficiency, although clearly both impact minimization and
process optimization, which are legitimate and complementary objectives
of green chemistry. Green chemistry applies to industrial prospects, organic
chemistry, inorganic chemistry, biochemistry, analytical chemistry, and
even physical chemistry.
The wide range of applications of green chemistry includes uses in the
pharmaceutical industry as well as new approaches that reduce or elimi-
nate the use of solvents or render them safer and more efficient. Green
chemistry has also inspired a growing number of ways to synthesize tradi-
tionally petroleum-based chemicals from biological materials, such as
using plant matter or waste.
Heterocyclic compounds are of very much interest in our daily life. They
have a high significance in our living system. Heterocyclic compounds have
a wide range of applications in agrochemicals, pharmaceuticals, veterinary
products, etc. They are also used as a starting material in the synthesis of
organic compounds. These compounds may be aromatic or anti-aromatic.
Heterocyclic compounds widely found in nature, e.g., pyramiding and
purine, are the parts of DNA, vitamins, and enzymes. This book focuses
on the importance of heterocyclic compounds in our life in different ways.
On the other hand, heterocyclic rings are present in the majority of
known natural products, contributing to enormous structural diversity.
In addition, they often possess significant biological activity. Medicinal
chemists have embraced this last property in designing most of the small
molecule drugs in use today.
Heterocyclic chemistry comprises at least half of all organic chemistry
research worldwide. This book covers the general properties of heterocyclic
xx Preface

compounds and general methods for their preparation. It provides the

basis for understanding the chemistry of individual ring systems that are
described in different chapters.
Heterocyclic compounds are an important class of molecules in organic
chemistry, due to their presence in natural products and their use in phar-
maceuticals and new materials.
Meanwhile, heterocyclic compounds play a vital role in the metabolism
of living cells. The range of known compounds is enormous, encompassing
the whole spectrum of physical, chemical, and biological properties.
This research-oriented volume is ideal for readers who want to fully
realize the almost limitless potential to discover new and effective phar-
maceuticals among heterocyclic compounds, the largest and most varied
family of organic compounds. The book features several case studies and
step-by-step descriptions of synthetic methods and practical techniques. It
also serves as a guide for chemists, offering them new insights and new
paths to explore for effective drug discovery.
The book introduces a selection of important heterocyclic compounds
and the vital role that they play in life.
This book provides a balanced, concise, and informative account of
heterocyclic chemistry that will be suitable for graduate students and a
convenient reference book for research workers, for both specialists in the
field and those whose expertise lies in other areas but who nevertheless
need information on green chemistry heterocyclic compounds.
This research-oriented book is illustrated throughout with clearly
drawn chemical structures. The highly systematic coverage given to the
subject makes this the most authoritative one-volume account of modern
green chemistry and heterocyclic compounds available. It also provides a
balanced, concise, and informative account of heterocyclic chemistry.
CHAPTER 1

AN OVERVIEW OF THE
ORGANIC SYNTHESIS AND
TRANSFORMATIONS INITIATED
BY SULFATE RADICAL ANIONS
(SO4•–) PRODUCED FROM AQUEOUS
PERSULFATE SOLUTIONS UNDER
TRANSITION METAL-FREE
CONDITIONS
PRIYA and PALANI NATARAJAN*
Department of Chemistry and Center for Advanced Studies in
Chemistry, Punjab University, Chandigarh, India
Corresponding author. E-mail: [email protected]
*

ABSTRACT

In recent times, the sulfate radical anions (SO4•−) are largely being utilized
for the functionalization of drugs (taxol, pregabalin, nicotine, etc.) and
synthesis of various organic compounds including heterocyclic compounds,
fertilizers, nanoparticles, and polymers. Moreover, they are also employed
for the destruction of a variety of organic contaminants such as perfluoro
carboxylic acids, chlorinated solvents, polycyclic aromatic hydrocarbons,
textile dyes, pharmaceuticals, xylenes, and so on. SO4•− have a very strong
one-electron oxidation potential, i.e., 2.43 V vs. NHE in aqueous solu-
tions, and they are well generated through the scission of the peroxide
bond of persulfates. To date, some important reviews are available that
2 Modern Green Chemistry and Heterocyclic Compounds

summarize the metal-catalyzed productions of SO4•− and their applications

toward organic functional group transformations as well as the extinction
of organic pollutants. To the best of our knowledge, however, there is still
no article exclusively discourses about the transition metal-free forma-
tion of SO4•− in aqueous solutions and their applications for the organic
synthesis and functional group transformations. Therefore, in this chapter,
we provide an overview of the transition metal-free protocols deal with the
generation of SO4•− from persulfates in aqueous media. Also, we highlight
the utilization of in situ formed SO4•− toward syntheses and functionaliza-
tion of various small organic molecules.

1.1 INTRODUCTION

In recent times, sulfate radical anion (SO4•−) has largely been utilized by
academicians and industrialists in a broad range of chemical processes
such as polymerization, soil remediation, and chemical oxidation for
groundwater treatment, organic transformations, and syntheses. The
sulfate radical anion is a very strong one-electron oxidant with an esti-
mated reduction potential of 2.43 V vs. NHE in aqueous media. Normally,
such a redox-activity is found only in (heavy) metals. This parallelism
of properties enables the replacement of traditional metal-based mate-
rials with sulfate radical anions (SO4•−). In addition, the use of SO4•− as
a reagent has many advantages, including mild reaction conditions, ease
of use, environmental-friendly, high tolerance towards functional groups,
astonishing solubility in water and other aqueous solvents like acetone,
acetonitrile, and alcohols.
The chemistry of SO4•− has been reviewed from time to time.
Recently, two review articles on transition metal-catalyzed productions
of SO4•− and their applications toward organic functional group transfor-
mations, as well as destruct of organic pollutants, have been compiled.
In this chapter, we provide an overview of the transition metal-free
protocols deal with the generation of SO4•− from persulfates in aqueous
media. Also, we highlight the utilization of in situ formed SO4•− toward
syntheses and functionalization of various organic compounds. The
(radical) reactions, especially free from transition metals and occur
in aqueous solutions, have attracted great attention of chemists due
to environmental friendliness. In addition, residual transition-metal
An Overview of the Organic Synthesis and Transformations 3

contamination could adversely affect the biological properties of the

final products.
Generally, the SO4•− initiate organic reactions through either of hydrogen
abstraction, one-electron oxidation, oxidative-decarboxylation, and hydrogen
abstraction followed by decarboxylation. Accordingly, this chapter has been
divided into four sections:

1. Hydrogen abstraction by sulfate radical anion;

2. Hydrogen abstraction by sulfate radical anion followed by
decarboxylation;
3. One-electron oxidation by sulfate radical anion; and
4. Indirect involvement of sulfate radical anion in organic synthesis.

1.2 GENERATION OF SULFATE RADICAL ANIONS (SO4•−) FROM

PERSULFATES

Persulfates (S2O82–) are low priced crystalline solids, stable, non-hygro-

scopic, soluble in aqueous solutions, and ecologically friendly oxidants
with high reduction potential. Regardless of high reduction potential,
persulfates in their native form are inactive and usually give no reac-
tion. For enhanced reactivity, they are activated through cleavage of O-O
bond either by the Fenton redox process (Eq. 1) or thermolysis (Eq. 2)
or photolysis (Eq. 2). Notice that the homolytic cleavage (Eq. 2) of O-O
bond of persulfates affords two SO4•− whereas heterolytic cleavage (Eq. 1)
provides one sulfate radical anion and one sulfate ion. Normally, the
persulfates in the form of Na2S2O8, K2S2O8, and (NH4)2S2O8 are highly
used as a reagent due to their ready availability in markets.
4 Modern Green Chemistry and Heterocyclic Compounds

1.3 HYDROGEN ATOM ABSTRACTION BY SULFATE RADICAL

ANION

1.3.1 FUNCTIONALIZATION OF N-HETEROCYCLIC

COMPOUNDS THROUGH HYDROGEN ATOM ABSTRACTION
BY SULFATE RADICAL ANION

The heterocyclic center is the significant theme of the vast majority of

commercial drugs because of their natural biological properties. It is
widely used to fight against numerous neurotic and physiological infir-
mities. These days, C-C bond arrangement by means of C-H function-
alization through cross dehydrogenative coupling is becoming quite an
alluring tool for the syntheses of imperative organic compounds as it is
atom and step economical. Understanding this approach, Shi et al. in 2013
(Scheme 1.1) [1] developed a transition metal-free, green approach for the
synthesis of substituted pyridines (18). Shi protocol worked by the reac-
tion of unprotonated pyridine derivatives (1) with 1,4-dioxane (8) by using
K2S2O8 as an oxidant in aqueous solution in the absence of any harmful
acid or toxic metal [1].
A variety of substituted pyridine derivatives (18a) were combined with
1,4-dioxane; however, non-substituted one provided the trisubstituted
product (18b). The electron-donating substituents (18c) on the pyridine
ring gave lower yields when contrasted with the electron-withdrawing
ones (18d). The pyridine ring with cyano- as a substituent indicated diverse
reactivities under the same reaction conditions such that C-2 substituted
cyano (18e) afforded mixture of mono substituents in 45% yield, C-4 (18f),
and C-3 (18g) cyano pyridine gave di- and tri-substituted products in 65%
and 61% yields, respectively [1].
Along with pyridines, the enormous literature is available on the C-H
functionalization of other heteroarenes. Singh and collaborators in 2015
(Scheme 1.1) [2] built up an exceptionally productive green methodology
for the coupling of alicyclic ethers (9), cyclic ethers and alkanes (8) with
diverse electron-deficient heteroarenes like pyridine (1), quinoline (2),
isoquinoline (3), pyrazine (4) and pyrimidine (7) in admirable yields. The
reaction continued under transition metal-free conditions in an aqueous
solution of acetone, avoiding the utilization of any acid that was earlier
required for the protonation of N-heteroarenes [2].
An Overview of the Organic Synthesis and Transformations 5

The reaction protocol was further stretched out to naphthoquinones

(10). Pyridines (18h), Quinolines (28a), isoquinolines (38a), pyrazine (48a)
gave high yields up to 90% with cyclic ethers. In the case of pyrimidine
(78a), the mixture of mono and disubstituted products were obtained. With
alkanes (78a) or alicyclic ethers (39a), the reaction yield was enhanced by
the addition of TBAB in DCE: water mixture [2]. Several control experi-
ments with radical scavenger like TEMPO confirmed the radical mecha-
nism as reaction yield reduced to a great extent in its presence.
Later in 2016, Shah and Dewari (Scheme 1.1) [3] reported a similar
convention for the C-H arylation of ethers using CFL light as irradia-
tion sources. The reaction continued at room temperature by means of
dual C(sp2)–H and C(sp3)–H functionalization through the HAT pathway
leading to the synthesis of N-heterocycles [3]. In the prior works revealed
by Minisci, the acidic catalyst was essentially utilized for the proton-
ation of heteroarenes, but, in this reaction, the yield is 77% even without
utilizing trifluoroacetic acid, along these lines, it was expected that proton-
ation of amines was likely happened through in situ generations of H+ ions
from water.
This convention was compliant to the assortment of electron-deficient
N-heteroarenes, for example, pyridines (1), quinolines (2), isoquinolines
(3), pyrazines (4), quinoxalines (5) and it was further extended to the prep-
aration of functionalized benzothiazoles (6) and naphthoquinones (10) [3].
The variety of cyclic (8) and non-cyclic ethers (9) was explored, and the
best outcomes were acquired with 1,4-dioxane. It was discovered that
1,2-dimethoxyethane with isoquinolines (38b) yielded regiomers where
arylation occurred at methylene C-H and methoxy C-H positions. Simi-
larly, yield up to 61% was obtained with benzothiazole (68a). Substituted
pyridines (18i) also reacted well with 1,4-dioxane.
In 2016, Zhang et al. (Scheme 1.1) [4] envisioned the cross dehydro-
genative coupling reaction of benzothiazole (6) with ethers in the biphasic
solvent mixture of water and ether at 29°C. The reaction proceeded in
visible light by making use of household 26W CFL bulb as irradiation
sources [4].
Similarly, in 2016, Barriault, and coworkers [5] detailed the oxidative
C(sp2)H and C(sp3)H cross-coupling reaction amongst heteroarenes and
unactivated ethers (Scheme 1.1) [5]. According to the substrate scope, best
outcomes were obtained with ether substituted pyridine (18j), quinoline
(28c), isoquinoline (38c, 39b), and pyrazine (48c) [5].
Another Random Scribd Document
with Unrelated Content
April 4, 1865, for wounds received in action. May 25, 1864. Mustered
out, Sept. 18, 1864 — expiration of term. Drafted— mustered out
with Co., July 16, 1865. Drafted — absent, sick, at muster out.
Absent, wounded, at muster out. Mustered out, Sept. 18, 1864 —
expiration of term. Mustered out, Sept. 18, 1864 — expiration of
term. Mustered out with company, July 16, 1865 — Vet. Mustered
out with company, July 16, 1865 — Vet. Mustered out with company,
July 16, 1865 — Vet. Drafted -mustered out with Co., July 16, 1865.
Drafted — mustered out with Co., July 16, 1865. Drafted— mustered
out with Co., July 16, 1865. Mustered out, Sept. 18, 1864—
expiration of term. Discharged December 4, 1862, for wounds
received in action. Discharired on Surgeon's certificate, June 17, '62.
Transferred to Vet. Reserve Corps, Dec. 23, 1864. Drafted— deserted
June 8, 1865. INIustered out with company, July 16, 1865. Mustered
out with company, July 16, 1865. Mustered out with company, July
16, 1865. Drafted— mustered out with Co., July 16, 1865 Drafted—
mustered out with Co., July 16, 1865. Drafted — mustered out with
Co., July 16, 1865. Drafted— mustered out with Co., July 16, 1865.
Mustered out, July 16, 1865. Drafted — absent, sick, at muster out.
Drafted— mustered oitt, July 11, 1865. Discharged on Surgeon's
certificate, Dec. 14, '61. Discliarged on Surgeon's certificate, Dec. 4,
'62. Drafted— disch. June 26, '65, by General Order. Transferred to
Vet. Reserve Corps, Oct. 29, 1864. Died March 26, 1862, of wounds
received at Winchester, Va., May 25, 1862. Killed at Cedar Mountain,
Va., August 9, 1862. Died at Pittsburg, Pa., March 7, 1864. Died at
Nashville, Tenn., October 17, 1864. Died at David's Island, N. Y., May
5, '64— buried in Cypress Hill Cemetery, L. I. Deserted June 26,
1865. Drafted — deserted June 7, 1865. INIustered out, Sept. 18,
1864— expiration of term. Drafted— disch. June 19, 1865, by
General Order. Discharged on Surgeon's certificate, Dec. 4, 1862.
Killed at Cedar Mountain, Va., August 9, 1862. Killed at Dallas, Ga.,
May 2,5, 1864. Drafted— mustered out with Co., July 16, 1865.
Drafted— mustered out with Co., July 16, 1865. Drafted— mustered
out with Co., July 16, 1865. Drafted — mustered out with Co., July
16, 1865. Drafted — mustered out with Co., July 16, 1865.
Discharged on Surgeon's certificate, Feb. 10, '62. Discharged on
Surgeon's certificate, June 17, '62. Mustered out, Sept. IS, 1864 —
expiration of term. Mustered out, Sept. IS, 1864 — expiration of
term. Drafted— deserted June 20, 1865. Drafted— mustered out
with Co., July 16, 1865.
 THREE YEARS' SERVICE. 1137 Company G. recruited in
potter county. James H. Graves Dennis H. Chesebro Wm. L.
Shattuck. Truman Bacon.... James M. MillerHorace C. Jones .. James
H. Cole., H. M. Rathbone Consider E. Lovell Jerome B. Stewart Jas. T.
Lockwood. William R. Clark. Geo. S. Kennedy... Xiuther Brizzee ....
John C. Wilkinson Chas. A. Estes Hosea B. Harris.... C. C.
Cavanaugh. E. A. Richmond.. Wells Kenyon Geo. Markham. James P.
M'Kee O. M. Cavanaugh... Francis W. Lovell.. Gilbert N. Manning EliG.
Lovell Noyes Snyder Geo. W. Pearsall.... Josiah T. Rathbone Hiram H.
Chesebro James Kenyon. William J. Brown.. George H. Barnes...
Samuel C. Grace Thomas Kenyon George Washington Lester Stone
Jay Chesebro James Livermore... Ayres, S. Freeman Armstrong,
Noah G Capt.... ..do .do. 1st. Lt. ..do ..do .do. 2d Lt .. 1st Sgt,
..do.... Serg't. .do. .do. .do. .do. .do. .do. ..do Corp.... ..do ..do. ..do.
..do. ..do. ..do. .do .do .do .do .do .do .do .do .do Muc ..do ..do ..do
Private do ! Sept. 13, '61, Sept. 13, '61, Sept. 13, '61, Sept. 13, '61,
Aug. 26, '62, Aug. 17, '61, Sept. 13, '61, Sept. 12, '61, Jan. 13, '64,
Sept. 13, '61, Jan. 13, '64, Jan. 13, '64, Feb. 2, '64, Jan. 13, '64,
Sept. 13, '61, Sept. 13, '61, Jan. 13, '64, Jan. 13, '64, Jan. 13, '64,
Jan. 13, '64, Jan. 13, '64, July 26, '63, Mar. 30, '64, Jan. 13, '64, Jan.
13, '64, do Jan. 13, '64, Sept. Sept. Sept. Julv July Sept. Sept. Sept.
Sept. Sept. Sept. July Aug. Mar. July 13, '61, 13, '61, 13. '61, 12, '62,
12, '62, 13, '61, 13, '61, 4, '63, 13, '61, 13, '61, 13, '63, 12, '62, 20,
'62, 17, '64, 12, '62, Annis, William |...do | Mar. 17, '63, 143
Resigned October 5, 1862. Pr. from Com. Serg't to Captain, Nov. 1,
1862— killed at Dallas, Ga., May 25, 1864. Pr. from 1st Sgt. to 2d Lt.,
Mar. 21, '64— to Capt., July 27, '64— prisoner from Aug. 9, to Sept.
18, '62— mus. out with Co., July 16, 1865— Vet. Regig-ned
September 11, 1862. Died at Harrisburg, Pa., June 18, 1863. Pr. from
priv. Co. C, to 2d Lt., Mar. 4, 1862— to 1st Lt., Sept. 1, 1863—
resigned Oct., 1864. Prisoner from May 2, to May 15, 1863 — pr.
from Sgt. to 1st Sgt., May 21, 1864— to 2d Lt., Aug. 23, 1864— to
1st Lieut., May 22, 1865— mustered out with company, July 16,
1865 — Vet. Discharged February 15, 1862. Prisoner from Aug. 9, to
Sept. 18, 1862— pr. from Serg't to 1st Serg't, Aug. 23, 1864— com.
2d Lt., July 15, '65 — not mustered — mustered out with cornpany,
July 16, 1865 — Vet. Discharged on Surgeon's certificate, Dec. 12,
'62. Prisoner from May 2, to May 15, 1863 — pr. from Corporal to
Sergeant, Sept. 29, 1864— mustered out with company, July 16,
1865— Vet. Pr, from Corporal to Sergeant, Oct. 13, '64— mustered
out with company, July 16, 1865— Vet. Pr. from Corporal to
Sergeant, Sept. 15, '64— mustered out with company, July 16, 1865
— Vet. Pr. from Corporal to Sergeant, Nov. 15, '64— mustered out
with company, July 16, 1865 — Vet. Discharged on Surgeon's
certificate. May 22, '62. Mustered out, Sept. 18, *64— expiration of
term. Died July 27, '64, of wounds received in action, July 20, 1864
— Vet. Killed in action, July 20, 1864— Vet. ]\Iustered out with
company, July 16, 1865— Vet. Pr. to Cor., Sept. 29, 1864— prisoner
from May 2, to May 15, 1863— mustered out with company, Julv i6,
1865— Vet. Prisoner from Aug. 9, to Sept. 18, '62— promoted to
Corporal, September 29, 1864— mustered out with company, July
16, ] 865— Vet. Sub.— pr. to Corporal, April 12, 1865— mustered
out with company, July 16, 1865. Promoted to Corporal, Nov. 1,
1864— mustered out with company, July 16, 1865. Prisoner from
May 2, to May 15, 1863 — promoted to Corporal, July 1, 1865—
mustered out with company, July 16, 1865— Vet. Promoted to
Corporal, July 1, 1865— mustered out with company, July 16, 1865
— Vet. Prisoner from Aug. 9, to Sept. 17, '62— mustered out. May 3,
1865— Vet. Disch. for wds. received in action, April 26, 1862.
Mustered out, Sept. 18, '64— expiration of term. Discharged on
Surgeon's certificate, Feb. 10, '63. Discharged by General Order,
June 8, 1865. Discharged by General Order, June 8, 1865.
Discharged on Surgeon's certificate, June, 1862. Killed by railroad
accident, December 11, 1863. Siib.— died Apr. 11, '65— bu. record,
Apr. 16, '65. Deserted January 19, 1863. Discharged on Surgeon's
certificate, Feb. 4, '63. Disch. on Surgeon's certificate — date
unknown. Discharged by General Order, June 8, 1865. Discharged by
General Order, June 8, 1865. Mustered out by General Order, June
15, 1865. Discharced Dec. 17, 1862, for wounds received at
Antietam, Md., September 17, 1862. Discharged by General Order,
June 21, 1865.
 1138 FORTY-SIXTH REGIMENT, Andrews, Silas Andrews,
Simeon G Belcher, Samuel Bradley, George W Bur dick, Albert D.
Bartges, Solomon I Boyle, George Black, Martin Brooks, Albert A ..
Brizzee, Edward ... Beatman, Peter Bryan, Simon Brad Shaw, Edward
Briggs, Leonard.... Bryan, Chauncey... Baily, Eli , Brooks, Hosea B
Brigham, Collins S Bradley, Nathaniel ...do. ..do. ..do. ..do. ..do. ..do.
..do. ..do. ..do. ..do. ..do. ..do. ..do. ..do. ..do. ..do. Brizzee, Wm. J.
Burton, Rosswell Brizzee, Freeman Brockway, Napol'n Bosworth,
James A Briggs, William I . Crawford, John W. Carnagey, William
Cotton, Thomas Cobb, Edward A... Cole, Cassius M„... Crane, Abelina
Cummings, Henry, Clark, John W Collar, Reuben Dwight, Wm. W...
Dennis, John Dickson, James Eastman, Leander Earl, William M....
Evans, Albert Estes, Lorenzo D ... Everett, Richard J Gilbert,
Edward..., Goodnoe, Abram...., Gilbert, Charles A., Goffe, Alva A
Graham, Ichabod.., Graves, Ezra A Garnett, Daniel S .., Green, John
W , Higley, Alfred N .., Hunter, Samuel .... Hill, Amos Hodge, William
A. Hopkins, Oliver C. Healy, John S Harris, Robert P... Hysong,
William HUl, Alexander D.. Hay, John Harris, John Hoy, Charles ...,
Holliday, Alexan'r Hoyle, James... Private do do .do. ..do. ..do. ..do.
..do. ..do. ..do. ..do. ..do. ..do. ..do. ..do. •:?§: .do. .do. .do. .do.
.do. .do. .do. .do.... .do.... .do.... .do.... .do.... .do.... .do.... .do....
.do.... ..do. ..do. ..do. ..do. ..do. ..do. .do. Mar. 30, '64, Sept. 13, '61,
Jan. 13, '64, Mar. Mar. July Aug. Feb. Mar. Mar. Sept. Sept. Sept.
Sept. July Sept. Mar. Sept. July 14, '64, 3, '64, 27, '6.3, 17, '63, 4,
'65, 15, '65, 14, '64, 13, '61, 13, '61, 13, '61, 13, '61, 12, '62, 14,
'63, 15, '65, 13; '61, 12, '62, Jan. 13, '64, Mar. 3, Sept. 13, Sept. 13,
Mar. 3, Jan. 13, July 27, July 27, Sept. 12, Sept. 13, Aug. 20, Sept.
13, Mar. 13, Feb. 27, Sept. 13, Mar. 30, Mar. 3, Sept. 12, Jan. 12,
Mar. 30, July 27, Mar. 14, '64, Mar. 14, '64 Jan. 13, '64, Mar. 14, '64:
Oct. 13, '61 Sept. 13, '61, Aug. 20, '62, Sept. 13, '61 Sept. 13, '61,
July 13, '63 Mar. 3, '64 July 30, '63 Mar. 3, '64 Sept. 13, '61 Sept. 13,
'61 Sept. 13, '61 Sept. 13, '61 ..do July 13, '63, ..do Mar. 14, '64: ,do
July 12, '62 Jan. 13, '64 .do .do .do .do Ingraham,Mar'nH ,..do Sept.
13, '61 Jackson, Thomas do Mar. 17, '64, Sept. 17, '63, Feb. 3, '65,
Discharged on Surgeon's certificate, May 3, '65^ Deserted August
18, 1862. Prisoner from April 14, to April 28, 1865— mustered out
with company, July 16, 1865 — Vet. Mustered out with company,
July 16, 1865. Mustered out with company, July 16, 1865. Substitute
— mustered out with Co., July 16, '65. Drafted— mustered out with
Co., July 16, 1865. Substitute— mustered out with Co., July IG, '65.
Drafted— mustered out with Co.. July 16, 1865. Mustered out, June
7, 1865, by General Order. Discharged on Surgeon's certificate, Dec.
16, '61. Disch. on Surgeon's certificate — date-unknown. Disch. on
Surgeon's certificate- date unknown. Discharged on Surgeon's
certificate, Sept. 29, '62. Discharged on Surgeon's certificate, Dec. 6,
1862. Substitute— discharged June 8, 1865, by G. O. Drafted—
discharged June 27, 1865, by G. O. Died at Strasburg, Va., Ma^ 20,
1862. Died Nov. 3, 1862, of wds. rec'd at Cedar Mountain, Va. , Aug.
9, 1862— buried in Cs^ress Hill Cemetery, Long Island. Wd. in
action, June 22, 1864— died July 4, 1864— buried at Chattanooga,
Tenn.— grave, 391. Died May 15, 1864. Deserted January 19, 1863.
Deserted July 2, 1863. Discharged July 16, 1865. Not on muster-out
roll — Vet. Substitute — mustered out with Co., July 16, '65. Drafted
— mustered out with Co., July 16, 1865. Substitute — absent, sick,
at muster out. Discharged on Surgeon's certificate, July, 1862. Disch.
on Surgeon's certificate — date unknown. Transferred to Vet. Res.
Corps, Nov., 1863. Killed in action, July 20, 1864. Died October 27,
1864. Deserted — date unknown. Mustered out with company, July
16, 1865. Mustered out with company, July 16, 1865. Drafted—
mustered out with Co., July 16, 1865. Mustered out with company,
July 16, 1865— Vet. Mustered out, July 10, 1865, by General Order.
Drafted— wounded in action, July 20, '64— mustered out, July 29,
1865. Discharged May 18, 1865, by General Order. Died at Stone
lliver, Aug. 4, 1864— grave, 440. Mustered out with company, July
16, 186.5— Vet. Mustered out with company, July 16, 1865.
Discharged on Surgeon's certificate, Dec. 30, '61. Discharged on
Surgeon's certificate, Nov. 2, '62. Discharged on Surgeon's
certificate, Jan. 15, '63. Mustered out, Sept. 18, 1864— expiration of
term. Died at Winchester, Va., May, 1862— buried iu National
Cemetery— lot, 9. Drafted— died September 18, 1864. Mustered out
with company, July 16, 1865. Drafted— mustered out with Co., July
16, 1865. Absent, sick, at muster out. Disch. for wds. rec'd in action
— date unknown. Disch. on Surgeon's certificate— date unknown.
Discharged on Surgeon's certificate, Oct. 25, '62. Discharged
November 13, 1862, for wounds received at Cedar Mountain, Va.,
Aug. 9, 1862. Drafted^disch. on Surg, certificate, Nov., 1863.
Discharged June 21, 1805, by General Order. Died Aug. 11, 1862, of
wounds received at Cedar Mountain, Va., Aug. 9, 1862. Died Dec.
21, '64, of wds. rec'd in action— Vet. Drafted— deserted March,
1864. Deserted Jane 3, 1865. Died Oct. 4, 1863— buried at
Alexandria, Va.— grave, 977. Discharged on Surgeon's certificate,
Jan. 15, '63. Mustered out with company, July 16, 1865.
 THBBB YEAJRS' SERVICE. 1139 Jones, William Johnson,
Lafayette Kuhns. Paul King, Nathan W, Kenyon, Van Ren'r ELinsey,
Henry. Private ..do Keck, William.... Kenyon, Gilbert.. Kenyon,
Orson.... Kibbee, William Lambert, Albert H Lawton, Joseph Leach,
James H Longnecker, John.. Lyman, Isaac Meaner, James E... Mace,
Robert J. H.. Morgan, Jacob Miller, Benjamin... Mascho, David
Munson, Henry M.. Mygrautz, Lewis B Myers, Anthony Marsh, David
Manor, Walter Munson, Enos., MulhoUand, James Miller, Ebenezer....
M'Dermott, Patrick Nichols, Henry H... Nichols, Titus V Noble,
Solomon .... Nelson, Newton Olney, Franklin S... O'Connor, Fergus...
Palmatier, Caleb A.. Potts, David Phillips, Isaac Plants, Reuben
Phillips, Moses R... Poe, James M Phillips, John Pennoyer, Elias Reed,
Albert Reynolds, George.. Raught, Hiram L.. Reinhart, Joseph..
Robbins, Asher W. Rob bins, William.. Romigh, George.... Romigh,
Jacob Ryan, Martin V Staysa, Isaac C Smith, Samuel Sweet, Stephen
B.. Sheppard, Lorin.... Staysa, John G Swift, Andrew J.... Sackett,
Volney D... Signor, Henry M. Sheppard, Sidney C Swift, Cyrus A. W..
Springer, Jeremiah Seely, Isaac E Julv 27, '63, Oct. 13, '61, July 13,
'63, Jan. 18, '65, Sept. 1.3, '61, July 80, '63, Aug. 21, '63, Sept. 13,
'61, Mar. 15, '64, Sept. Jan. Mar. Mar. July Mar. July July July Jan.
Sept. Sept. July Feb. July July 13, '61, 13, '64, 14, '64, 14, '64, 13,
'63, 15, '65, 12, '63, 27, '63, 27, '63, 25, '65, 13, '61, 13, '61, 27, '63,
8, '65, 13, '63, 27, '63, Sept. 13, '61, Jan. 25, '65, Sept. 13, Sept. 13,
Sept. 13, Sept. 13, Mar. 17, July 29, Sept. 13, Sept. 11, Jan. 13, July
29, April 11, Sept. 13, Sept. 13, July 27, Mar. 14, Aug. 20, '62, Mar.
3, '64, July 13, '63, Jan. 18, '65, Sept. 13, '61, Sept. 13, '61, Sept.
13, '61, Feb. July Jan. Jan. July Mar. Mar. Sept. Sept. Sept. 10, '64,
25, '63, 13, '64, 13, '61, 13, '63, 1.5, '65, 15, '65, 13, '61, 13, '61,
13, '61, Sept. 13, '61, Mar. 5, '65, Jan. 13, '64, Oct. 13, '61, Sept. 13,
'61, Drafted— mustered out with Co., July 16, 1865. Discharged Oct.
4, 1862, for wounds received in action. May 25, 1862. Drafted—
mustered out with Co., July 16, 1865. Drafted— mustered out with
Co., July 16, 1865. Mustered out. Sept. 13, 1865— expiration of
term. Drafted— discharged Dec. 26, 1864, for wounds received in
action, June 15, 1864. Drafted— discharged by G. O., June 21, 1865.
Died at Darnstown, Md., November 27, 1861. Died August 27, 1864
— buried at Chattanooga, Tenn. — grave, 510. Deserted — date
vmknown. Mustered out with company, July 16, 1865 — Vet.
Mustered out with company, July 16, 1865. Mustered out with
company, July 16, 1865. Substitute — mustered out with Co., July
16, '65. Drafted — mustered out with Co., July 16, 1865. Drafted —
mustered out with Co., July 16, 1865. Drafted— mustered out with
Co., July 16, 1865. Drafted— mustered out with Co., July 16, 1865.
Drafted — mustered out with Co. , July 16, 1865. Discharged on
Surgeon's certificate, Nov. 2, '62. Discharged on Surgeon's
certificate, Mar. 5, '63. Drafted— discharged by G. O., June 14, 1865.
Substitute— discharged by G. O., June 17, 1865. Drafted— died
August 7, 1864. Drafted— died August 1, 1864— buried at
Chattanooga, Tenn. — grave, 255. Captured at Winchester, Va., May
25, '62— died Aug. 6, '62— burial record, July 22, '62— buried at
Lynchburg, Va. Drafted— died June 16, 1865— buried in National
Cemetery, Arlington, Va. Deserted — date unknown. Killed at Cedar
Mountain, Va., Aug. 9, 1862. Discharged on Surgeon's certificate,
Nov. 25, '62. Discharged on Surgeon's certificate, Feb. 4, 1863.
Discharged by General Order, May 23, 1865. Drafted— killed in
action, July 20, 1864. Discharged on Surgeon's cert. — date
unknown. Drafted — disch. on Surgeon's certificate, 1864. Mustered
out with company, July 16, 1865 — Vet. Substitute — mustered out
with Co., July 16, '65. Substitute— mustered out with Co., July 16,
'65i. Discharged Sept. 18, 1864— expiration of term. Discharged on
Surgeon's certificate, Jan. 29, '64. Transferred to Vet. Res. Corps,
January 2, 1864. Died July 20, '64— buried at Chattanooga, Tenn. —
grave, 51. Deserted, January 19, 1863. Mustered out with company,
July 16, 1865. Drafted— mustered out with Co., July 16, 1865.
Drafted— mustered out with Co., July 16, 1865. Discharged on
Surgeon's cert.— date unknown. Discharged on Surgeon's certificate,
Sept. 1, 1862. Died Aug. 17, 1802, of wounds received at Cedar
Mountain, Va., August 9, 1862. Drafted— died July 18, '64, of wds.
rec. in action. Drafted— died Sept. 11, '64, of wds. rec. in action.
Died July 18C4, of wds. received in action— Vet. Mustered out with
company, July 16, 1865 — Vet. Drafted— mustered out with Co., July
16, 1865. Drafted— mustered out with Co., July 16, 1865. Drafted—
mustered out with Co., July 16, 1865. Discharged on Surgeon's cert.
— date iinknown. Discharged on Surgeon's certificate, 1862.
Discharged Nov. 7, 1862, for wounds received at Cedar Mountain,
Va., August 9, 1862. Discharged April 9, 1863, for wounds received
at Cedar Mountain, Va., August 9, 1862. Drafted— disch. by General
Order, June 27, 1865. Transferred to Vet. Res. Corps, Sept., 1864—
Vet. Died at Hagerstown, Md., March 17, 1862. Killed in action, April
26, 1862.
 1140 FOETY-SIXTH REGIMENT, NAME. BANK. DATE OF
MUSTER INTO SERVICE. 1 I 3 REIUABSS. Shaber, Asa Private Aug.
17, '6S, Drafted— died January 18, 1864. Snath, James H ...do Jan.
1.3, '64, 3 KUled in action, July 20, 1864— Vet. Smith, Fred'ck A...
...do Sept. 13, '61, 3 Deserted August 18, 1862. Simonds, John H...
...do Feb. 3, '6.5, 3 Deserted June 3, 1865. Terwilleger, Henry ...do
Jan. 13, '64, 3 { Wounded in action, May 25, 1864— absent, in
hospital, at muster out— Vet. Thompson, Thomas ...do July 13, '63,
3 ' Drafted— mustered out by G. O., July 5, 1865. Terwilleger, Joel....
...do Oct. 13, '61, 3 i Died of wds. rec. at Winchester, Va., May 25,
'62. Wyland, Jacob ...do Aug. 3, '63, 3 i Drafted— mus. out with
company, July 16, 1865. Whittaker, W. A... ...do Sept. 13, '61, 3
Discharged on Surg, certificate— date unknown Wallace, William J
...do Oct. 13, '61, 3 i Discharged on Surg, certificate— date
unknown. Williams. John ...do Mar. 3, '64, 3 1 Discharged by General
Order, June 30, 1865. Warner, Harvey J.. ...do Sept. 13, '61, 3 1
Killed at Winchester, Va., Mav 25, 1862. Walters, Frederick ...do July
28, '63, 3 Substitute— died April 25, 1865. Wilcox, WilUam.... ...do
Mar. 14, '64, 3 Captured June 22, 1864— died at Florence, Soutl 1
Carolina. 3 Killed at Cedar Mountain, August 9, 1862. Welch, Charles
...do Sept. 13, '61, Warner, Hiram P... ...do Sept. 13, '61, 3 Deserted
June 18, 1862. YounsT, Joseph ...do Aug. 14, '63, Sept. 20, '64, 3
Substitute— absent, in arrest, at muster out. Young, John E ...do....
1 Drafted— discharged by G. 0., June 8, 1865. Company H.
RECRUITED IN POTTER COUNTY. Wm. D. Widger Nathan'lJ. Mills..,
Alex. W. Selfridge Ii. Henninghauser.. Thos. B. Gorman .., Orlando J.
Reese... Norman M. Vance. Capt. ...do.. ...do.. 1st Lt. ..do.... George
W. White. Merrick Jackson... Chas. N. Barrett... Joseph H. Austin.
Bennev'le Schlegel.. Dan'l D. Tompkins Wm. P. Green... Charles Riant
ElnoE. Burdick... Clarendon Darling, Albert Reed Elisha S. Horton....
L. E. Sinsabaugh.. Daniel H. Judd W. Hollenback.. •lohn W. Axx....
.do ... .do.. 2dLt. ...do... .do .... 1st Sgt. Serg't . ...do.... ..,do.... .do.
.do. .do. .do. .do. .do. .do. Corp. ...do.. Sept. 13, '61, Sept. 13, '61,
Sept. 13, '61, Aug. 17, '61, Sept. 12, '61, Sept. 18, '61, Sept. 13, '61,
Sept. 13, '61, Sept. 13, '61, Sept. 13, '61, Mar. 27, '62, Jan. 13, '64,
Jan. 13, '64, Sept. 13, '61, Sept. 13, '61, Sept. 13, '61, Sept. 13, '61,
Jan. 13, '64, Sept. 13, '61, Sept. 13, '61, Jan. 13, '64, July 27, '63,
Resigned December 27, 1861. Pr. to Captain, Jan. 1, '62— disch.
June 24, 1862. Transferred from 28th reg. P. V. as 2d Lt., Feb. 21,
'62— pr. to Capt., Dec. 21, 1862— to Bv. Maj., Mar. 18, '65— mus.
out with Co., July 16, 1865. Resigned August 1, 1862. Promoted
from Sgt. Maj. to 1st Lt., Feb. 1, '62— discharged March 20, 1862.
Promoted from Com. Sgt. to 2d Lt., Dec. 19, '62— to 1st Lt., Feb.,
'63— dismissed Aug. 26, 1864. Promoted from Cor. to Sergt. , Dec.
6, '61 — ^to 1st Sgt.. March 20, '63— to 2d Lt., July 27, 1864— to
1st Lieutenant, December 18, 1864 — mustered out with company,
July 16, 1865 — Vet. Discharged February 1, 1862. Promoted to
Sgt., Oct. 30, '62— to 2d Lieut., June 17, 1863— dismissed May 2,
1864. Pr. from Cor. to Sst., Nov. 1, 1861— to 1st Sergt., Feb. 1, '62—
red. Nov. 1, 1862— pr. to 1st Sergt., Sept. 1, 1864— to 2d Lieut.,
Dec. 18, 1864— mustered out with company, July 16, 1865 — Vet.
Promoted to 1st Sgt., Sept. 2, 1861— died at Hancock, Md.,
Februarv 7, 1862. Pr. to Cor., Oct. 10, '63— to Sgt — to 1st Sgt., Jan.
5, '65— mus. out with Co., July 16, 1865— Vet. Pr. to Cor., Oct. 30,
'61— toSgt., Nov. 1, '62— mustered out with company, July 16, 1865
— Vet. Promoted to Sgt., Sept. 2, '61— red. Oct. 28, '62— promoted
to Sergt., Nov. 1, 1862— mustered out with company, July 16, 1865
— Vet. Pr. to Cor., Nov. 1, '62— to Sgt., Oct. 1, '63— mustered out
with company, July 16, 1865— Vet. Pr. to Cor., April 5, '64— to Sgt.,
July 6, '65— mustered out with company, July 16, 1865 — Vet.
Disch. on Surgeon's certificate — date unknown. Discharged on
Surgeon's certificate, Oct. 30, '62. Pr. to Cor., Nov. 1, '62— to Sgt.,
Jan, 5, '65— discharged by special order War Dep't — Vet. Pr. to
Cor.. July 28, '62— to Sergt., Nov. 1, 1863— mus. out, Sept. 18,
1864— expiration of term. Pr. to Sgt., Sept. 2, '61— died Nov., 1862
— bu. record, Nov. 12, '61, at Washington, D. C. — buried in Military
Asylum Cemetery. Promoted to Corporal, Nov. I, 1863 — mustered
out with company, July 16, 1865 — Vet. Drafted — promoted to Cor.,
Oct. 1, '64 — mustered out with company, July 16, 1865.
 THEEE YEAES' SERVICE. 1141 William A. Butler Oliver J.
Parker.... JohnG. Hollenback John S. King . Michael Dunn. Amos R.
Stillman. Allen Jordan. Geo. W. M. Heister Henry Rogers Charles H.
Rusher. Benjamin F. Bishop Henry J. Epler . James Quigley. Stephen
Darling., SethM'MuUin Philo S. Baker.. George A. Post.. Ransom R.
Higley. John W. Crosby Michael H. Mengis Milton Patterson...., Abr'm
G. Leonard.. Allen, Robert Ayres, Charles Anson, Robert M.... Adams,
John Baker, Luther S Baker, Isaac B Butier, Joseph Burdick, George
Beardsly, Ransom.. Baker, Alanson L... Bel din, Sylvester... Barr,
George W Bliss, Marcus A Bessey, Niles K Baker, David B Barber,
Augustin L Barber, Francis Cronk, Hannibal H Cain, Ebenezer Card,
William F:.... Cooper, George N ... Courtwright, Oren.. Courtwright, D
Conner, Lewis Chesebi-o, Dennis H Clark, Daniel Corl, Henry W
Crawford, Rob't M. Cone, Anson J Clinton, George Dickson, James
C... Dimraick, Ezra R... Dingman, William Dye, Anderson Dingman,
John Corp. ...do.. ...do.. ..do.... ..do.... ...do... Muc... ...do... ...do...
Pi'ivate ..do ..do ..do ..do ..do ..do ..do ..do ..do ..do ..do ..do ..do
..do ..do ..do ..do ..do ..do ..do ..do ..do ..do ..do Jan. 13, '64, Jan.
13, '64, Mar. 3, '64, July 24, '63, Jan. 13, '64, Mar. 3, '64, Sept. 1.3,
'61. Sept. £.3, '61, Sept. 13, '61, Sept. 13, '61, Dec. 81, '61, Feb. 20,
'62, July 27, '62, Sept. 13, '61, SQpt. 13, '61, Jan. -iM, '84, Jan.
IS.'sM, Sep*. IS, '01, Feb. Feb. Sept. July Sept. Sept. Mar. Jan. Jan.
Mar. Mar. Mar. Sent. Sept. Sept. Sept. Mar. Sept. Sept. Feb. Jan. Mar.
Sept. Mar. 15, '64, 15, '64, 13, '61, 29, '63, 13, '61, 13, '61, 3, '64,
13, '64, 13, '64, 3, '64, 17, '64, 1.5, '65, 13, '61, 13, '61, 13, '61, 14,
'63, 24, '61, 13, '61, 16, '63, 29, '64, 13, '64, 15, '65, 13, '61, 3, '64,
Sept. 13, '61, Sept. 13, '61, July 1, '62, Sept. 12, '61, Sept. 13, '61,
July 14, '63, July 17, '63, Aug., '61, Sept. 5, '64, Mar. 15, '65, Sept.
13, '64, Mar. 17, '64, July 14, '63, Mar. 17, '64, Promoted to Corporal,
November 1, 1,864— mustered out with company, July 16, 1865—
Vet. Promoted to Corporal, Mav 1, 18(35 — mustered out with
company, July 16, 1865— Vet. Promoted to Corporal, .June 25,
186.5— mustered out with company, July 16, 1865. Substitute—
promoted to'^Corporal, July 1, 1865 — mustered out with company,
July 16", 1865. Promoted to Cor., Oct. 1, '6.'5— wd. in action. May
25, '64 — absent, in hospital, at muster out — Vet. Promoted to
Corporal, June 30, 1864— mustered out by General Order, May 25,
1865. Discharged on Surgeon's certificate, Feb. 3, '65. Discharged
August 31, 1862. Discharged on Surgeon's certificate, Mar. 12, '63.
Promoted to Corporal, Feb., 186.3 — discharged for wounds received
in action. May 2, 1863. Discharged on Surgeon's certificate, Feb. 2,
'63. Promoted to Corporal, January 5, '65 — mustered out, March
25, 1865— expiration of term. Promoted to Corporal, Oct. 10, 1863
— discharged by General Order, June 8, 1865. Promoted to Corporal,
September 2, 1861— transferred to Veteran Reserve Corps, Auar. 8,
186.3. Promoted to Corporal, September 2, 1861- killed at
Winchester, Va., May 25, 1862. Promoted to Corporal, September 1,
'64 — died at Atlanta, Georgia, October 21, 1864— Vet. Pr. toCor.,
Nov. 1, '63— died July 29, '64, ofwds. rac. at Peach Tree Creek, Ga.,
July 20,'64— Vet. Promoted to Corporal, November 1, 1862 — died
at Alexandria, Virginia, February 27, 1864. Not on muster-out roll.
Mustered out with company, July 16, 1865. Mustered out with
company, July 16, 1865. Discharged on Surgeon's certificate, Dec. 6,
'62. Substitute — mustered out with Co., July 16, '65. Discharged on
Surgeon's certificate, Dec. 12, '62. Discharged on Surgeon's
certificate, Apr. 30, '62. Discharged on Surgeon's certificate, Feb. 3,
'65. Mustered out with company, July 16, 1865- Vet. Mustered out
with company, July 16, 1865— Vet. Mustered out with company, July
16, 18')5. Mustered out with company, July 16, 1865. Drafted—
mustered out with Co., "July 16, 1865. Mustered out, Sept. IS, 1864
— expiration of term. Discharged on Surgeon's certificate, 1862.
Died at "Hancock, Maryland, February 27, 1862. Drafted— died at
Decherd, Tenn., Oct. 18,'1863. Died at Atlanta, Georgia, October 26,
1864. Killed at Cedar Mountain, August 9, 1862. Drafted — deserted
June 2, 1865. Deserted March, 1864. Mustered out with company,
July 16, 186.5 — ^Vet. Drafted — mustered out with Co., July 16,
1865. Mustered out with company, July 16, 1865. Died May 28, 18';4
— buried at Chattanooga, Tennessee— grave, 511. Discharged on
Surgeon's certificate, June 5, '62. Discharged on Surgeon's
certificate, Oct. 7, '62. Discharged on Surgeon's certificate, April 26,
'63. Promoted to Commissary Sergeant, Aug. 1, 1862. Died August
20, 1862, of" wounds received at Cedar Mountain, Va.. August 9,
1862. Drafted — died May 18, 1864, of wounds received at Resaca,
Georgia, May 15, 1864. Drafted — killed "near Fayetteville,
Tennessee, Dec. 21, '63 — buried at Scone River — grave, 26. Not
mustered into United States service. Discharged by General Order,
June 8, 1865. Drafted — mustered out with Co., July 15, 1865.
Discharged on Surgeon's certificate, Apr. 23, '62. Discharged bv
Gerieral Order, June 8, 1865. Drafted— transferred to V. R. C, March
22, '65. Died at Nashville, Tennessee, June 25, 1864.
 1142 FOETY-SIXTH EEGIMBNT, Dereamir, John P...
Dereamir, Mahlon .. Eddy, Isaiah Ferrand, A. H Feaster, Henry
Fessenden, R. M.... Gray, Charles Green, James Gibson, John Green,
Stephen B... Homer, John Hart, Amos J HohTies, Wm. M.... Harrison,
Wm. H .. Havlin, John Hart, Jesse Hoffman, Fred. G... Jones, Pliilip L
James, WilUam Kelley, Edward E.. Kenyon, Geo. W Keighlinger, Geo.
S Lilley, Charles H... Luce, John Lamont, Olark A ... Lowrie, David B
Munnel, Robert E .. Marshall, John D... Muer, William Marshall, Nei
Mills, Thomas J ..... Mead, Philip Miller, Pasco M Mushall, James C...
Miles, Chester Morrison, Sylvester M'Candless, H. L... M'Coy,
Benjamin F M'Cahan, John D... Nelson, Charles S... Nisbit, John
Ostrander, And. H Ostrander, E. D Oliver, John. Parker, Sidney L...
Preston, Richard N Pickering, A. D Peoples, Wm. L Post, Reuben M
Palmeter, Joseph J Persing. Reuben .... Peet, John Patterson, Samuel
. Palmeter, Nicholas Pratt, Horace R Quick, Luther P...., Rossman,
Orson ...., Rouse, Amos , Ramsey, Josiah A... Ryan, James I Richie,
David F.... Ross, William Roberts, James J.. Ross, Robert Reeves,
Charles Riand, Francis M.. Sheldon, Fred'k A Stillman, Birney...
Schlesser, Ephraim Scanloy, Andrew. Sno (grass, Wash...
Sinsabaugh, T. M. Mav July Mar. Feb. Mar. Mar. Mar. July Sept. Jan.
July Sept. Sept. July Sept. July Jan. Oct. Jan. Mar. Sept. Mar. 15,
Mar. 15, Sept. 13, Sept. 13, July 31, July 29, Jan. 13, July 31, Sepi
13, Sept. 13, Sept. 13, S9pt. 16, Mar. 11, July 14, Julv 27, July 14,
July 14, Mar. Mar. Mar. Mar. July Jan. .Jan. Sept. July Sept. Sept. Mar.
Sept. July Sept. Sept. Sept. Mar. July July Oct. July Jan. Sept. Sept,
Sept. Mar. Jan. Mar. Mar. Julv July Jan. Killed at Cedar Mountain, Va.,
Aug. 9, 1862. Killed at Kenesaw Mountain, June 16, 1864. Drafted —
mustered out with Co., July 16, 1865. Absent, sick, at muster out.
Discharged on Surgeon's certificate, June, 1862. Died at Louisville,
Ky., April 5, 1834. Mustered out with company, July 16, 1865.
Mustered out with company, July 16, 1865. Substitute — mus. out
with Co., July 16, 1865. Discharged on Surgeon's certificate, 1862.
Mustered out with company, July 16, 1865 — Vet. Drafted—
mustered out with Co., July 16, 1865. Drafted — absent, sick, at
muster out. Discharged by General Order, June 8, 1865. Drafted—
diseh. by General Order, June 8, 1865. Deserted January 18, 1862.
Deserted — date unknown. Wounded in action, December 18, 1864
— absent, in hospital, at muster out — Vet. Mis. in action at
Middletown, Va., May 25, 1862. Mustered out with company, July 16,
1865 — ^Vet. Mustered out with company, July 16, 1865. Drafted—
died at Chattanooga, Tenn., Aug. 8, 1864— burial record, Aug. 8,
1865— grave, 424. Drafted— mustered out with Co., July 16, 1865.
Drafted — absent, feick, at muster out. Mustered out, Sept. 13, '64
— expiration of term. Mustered out, Sept. 18, '64 — expiration of
term. Drafted— mustered out with Co., July 16, 1865. Drafted—
mustered out with Co., July 16, 1865. Absent, wounded, at muster
out — Vet. Drafted— absent, sick, at muster out. Mustered out,
Sept. IS, '64— expiration of term. Discharged by General Order, June
19, 1865. Discharged — date unknown. Drafted— transferred to V.
R. C, June 13, 1865. Died July 15, 1864. Drafted— killed at Resaca,
Ga., May 15, 1864. Drafted— mustered out by G. O., June 1, 1865.
Drafted— died at Alexandria, Va., Sept. 23, 1863. Substitute— died
July 25, '64, of wounds received at Peach Tree Creek, Ga., July 20,
1864. Mustered out with company, July 16, 1865. Mustered out with
company, July 16, 1865. Mustered out witli company, July 16, 1865.
Mustered out with company, July 16, 1865. Substitute— absent, sick,
at muster out. Mustered out with company, July 16, '65— Vet.
Absent, wouu'led, at muster out — Vet. Drafted — absent, sick, at
muster out. Drafted — absent, sick, at muster out. Discharged May
18, 1862. Discharged November 10, 1862. Discharged on Surgeon's
certificate, Apr. 18, '65. Died at Muddy Branch, Md., Dec. 21, 1861.
Drafted— died at Atlanta, Ga., Sept. 26, 1864. Killed at
Chancellorsville, Va., May 2, 1863. Drafted— killed at Pine Knob, Ga.,
June 15, '64. Discharged September, 1832. Mustered out with
company, July 16, 1865. Drafted— mus. out with company, July 16,
1865. Drafted — mus. out with company, July 16, 1865. Mustered
out, Sept. 13, 1864— expiration of term. Drafted— disch. on Surg,
certificate, Nov. 1, '64. Killed near Dallas, Ga., May 25, 1864— Vet.
Deserted July, 1862. Deserted July, 1863. Drafted— deserted June
21, 1865. Deserted September 19, 1864. Mustered out with
company, July 16, '65— Vet. Mustered out with company, July 16,
1865. Drafted— mus. out with company, July 16, 1865. Drafted—
mus. out with company, July 16, 1865. Drafted— mus. out with
company, July 16, 1865. Prisoner— mus. out with Co., July 16, '65—
Vet.
 THEEE YEARS' SERVICE. 1143 KAHE. RANK. DATE OF
MUSTER INTO SERVICE. -9 f REMARKS. Smith, Leizer Smith, William
Stoner, Henry F Swank, Charles Scoville, Ahnon C. Private ...do ...do
...do ...do ...do Mar. 14, '64, Sept. 13, '61, Sept. 13, '61, Feb. 28,
'62, Sept. 5, '64, Feb. 15, '6.5, July 27, '63, Mar, 3, '64, Jan. 13, '64,
Sept. 13, '61, 3 3 3 3 1 1 3 3 3 3 Absent, sick, at muster out.
Discharged— date unknown. Mustered out, Sept. 18, 1864—
expiration of term. Discharged on Surgeons certificate, Sept. 28, '62,
Discharged June 8, 1865, by General Order. Discharged Juno 28,
1865, by General Order. Drafted— died March 15, 186.-). Died at
Indianapolis, Ind., April 9, 1864. Deserted December 29, 1864— Vet.
Deserted June, 1862. Died— buried at Chattanooga, Tenn., grave,
569. Discharged June 8, 1865, bv General Order. Discharged June 8,
1865, by General Order. Discharged June 8, 1865, by General Order.
Mustered out with company, July 16. 1865. Drafted— mvistered out
with Co., July 16, 1865. Drafted— mustered out with Co., July 16,
1865. Absent, sick, at muster out. Discharged on Surgeon's
certificate, Oct. 3, 1862. Discharged on Surgeon's certificate. Mar.
20, '63. Died at Hancock, iNId., January 28, 1862. Drafted— killed at
Peach Tree Creek, Ga., July 20, 1864. Deserted June 30, 186.3—
returned April 16, 186.5again deserted June 21, 1865. Mustered out
with company. July 16, 1865. Killed at Cedar Mountain, Va., August
9, 1862. Steller, Adam Strong, Casaius M... Stukey, Emanl M..
Slayton, Henry C... ...do ...do ...do ...do . do . . Tuttle, Joseph .do
Sept. 5, '64, Sept. 5, '64, Sept. 5, '64, Mar. 3, '64, July 14, '63, Sept.
14, '63, Mar. 3, '64, Feb. 26, '62, Sept. 13, '61, Sept. 13, '61, Sept.
14, '63, Sept. 13, '61, Mar. 3, '64, Sept. 13, '61, 1 1 1 3 3 3 3 3 3 3 3
3 3 3 Vanmater, Jacob B. Vanmater, Jacob.... Wa'-jen, Cassrus Wolf,
Jacob H.. ...do ...do ...do do Wfti^ght, Charles W. Warren, Alfred H..
Wirt, William ...do ...do ...do Wykoff, Charles H. Ward, Andrew J....
Wright, Hezek'h J. Walker, Theo. L Younglove, Geo. S.. Yeomans,
Lewis H. ...do ...do ...do ...do ...do ...do Company I. RECRUITED IN
LUZERNE COUNTY. Richard Fitzgerald Patrick Griffith John Care
Joseph Matchett.. George W. Boyd.. JohnH. Knipe.... Robert Young..
.. .Tohn Auglun Samuel Chambers. Peter Van Kirk Lewis C. Eakraan.
Michael J. Hawley. John E. M'Carty... Oliver B. Simmons Jeremiah
Ryan Uriah Kern James M. Bigler. HughQuinan John Burke M. F.
ORourke.. Charles Hessley.. Anthony Goyle ... John D. Leclere....
Capt. ..do.. ..do.. ...do.. IsLt. ..do... .do. 2dLt. ...do... .do... IstSgt.
..do.... ..do.... ..do.... Serg't. ..do ..do .do. ...do.. ..do.. ..do.. Corp.
...do.. Oct. 31, Sept. 16, Oct. 31, Aug. 17, Sept. 17, Aug. 24, Oct.
31, Oct. 13, July 27, July 14, Oct. 13, Aug. 29, Mar. 1, Jan. 13, July
13, Feb. 29, Jan. 13, Oct. 31, Oct. 31, Oct. 31, Jan. 13, July 13, '61,
3 '61, 3 '61, 3 '61, 3 '61, 3 '62, 3 '61, 3 '61, 3 '61, 3 '64, 3 '63, 3 '61,
3 '62, 3 '62, 3 '64, 3 '63, 3 '64, 3 64, 3 61, 3 '61, 3 61, 3 '64, 3 '63, 3
Discharged February 15, 1862. Promoted to Major, August 1, 1863.
Promoted from 1st Lieutenant to Captain, Aug. 17j 1863— resigned
June 10, 1864. Pr. fr. 1st Lt. of Co. C. to Capt., July 27, 1864 —
mustered out with company, July 16, 1865. Promoted to Adjutant,
September 17, 1861. Pr. fr. priv. Co. B, Aug. 5, '63 — died of wounds
received at Resaca, Ga., May 15, 1864. Pr. fr. Sgt. to 2d Lt., Jan. 15,
'63, to 1st Lt., Nov. 12, 1864 — mustered out. May 15, 1865, by
order War Department. Discharged February 15, 1862. Resigned
January 22, 1863. Pr. to Sgt., Oct. 10, '62— to 2d Lt., July 27, '64—
mustered out with company, July 16, '65 — Vet. Drafted— pr. to Cor.,
Sept. 10, 1863— to Sgt., Sept. 1, ]864— to 1st Sgt., June 8, 186.5—
com. 1st Lt., July 15, 1865— "not mustered — mustered out with
company, July 16, 1865. Mustered out,"Sept. 18, '64 — expiration of
term. Discharged June 8, 1865, bv General Order. Promoted to 2d Lt.
of Co. D, October 9, lSi32. Promoted to Cor., Nov. 10, 1863— to Sgt.,
Sept. 1, 1864— mus. out with Co., July 16, 18(j5— Vet. Drafted— pr.
to Cor., April 1, '64— to Sgt,, Nov. 1, 1864— mustered out with Co.,
July 16, 1865. Promoted to Cor., Sept. 1, 1864— to Sgt., Nov. 1, 186-
1 — mustered out with Co., July 16, 1865. Promoted to Cor., Nov. 1,
1S64— to Sgt., June 8, 1865— mus. out with Co., July 16, 1865—
Vet. Mustered out, Sept. IS, 1864— expiration of term. Discharged
on Surgeon's certificate. Feb. 9, 1863 Killed at Antietam, September
17, 1862. Promoted to Corporal, November 29, 1863- mustered out
with compan3^, July 16, 1865 — Vet. Drafted — promoted to
Corporal, Sept. 1, 1864— mustered out with company, July 16,
1865.
 1144 FOETY-SIXTH EEGIMENT, Wm. T. Smith.... Thomas
M'Lane. Henry S. Kern. .. Geo. W.Arnold.. Henry Booth , WilUam H.
Booth. Henry Schlepe Patrick Clark James Kevlin Richard Mallory.,
Henry Runge John Homer , Dennis Carney.... Henry E. Gould..
Lyman Moore John M'Comb Ammann, John.... Anderson, J Awe,
Peter Bates, John Ballentine, Wm.... Barnes, Henry G. . Burkey,John
Ballentine, John... Bly stone, Henry... Barrett, James Bowman,
Jacob. Burke, Anthony... Bush, Israel Bushell, Charles.., Burke,
Patrick Bush, Leander Cannavan, Henry... Clark, John Cassidy,
Patrick Corcoran, Thomas.. Cain, Barney.......... Cain, Patrick Crow,
Geo. W Coughlan, Wm Carrigan, Peter Clark, Michael Calhoun,
James Clary, Jolm D Dickey, Henry Dowling, M. A Duncan, James
Devine, Patrick Davis, Henry Etter, George H Frederick, James...
Flynn, Peter Fisher, Silas Fullum, Benjamin.. Freeburn, John M..
FuUerton, Harvey.. Frank, Alex. G Fox, James ,. Fisher, John Corp.
...do.. ...do.. ...do.. ..do ..do ..do ..do.... ..do„.. ..do ..do.... Muc...
..do ...do Private ...do ...do ...do ...do ...do ...do ...do ...do ...do do
do do ...do ...do ...do ...do ...do ...do ...do ...do ...do ...do ...do ...do
...do ...do ...do ...do ..do ...do ...do ...do ...do ...do ...do ...do July
13, Mar. 0, July 13, Mar. 9, Jan. 13, Mar. 31, Oct. Oct. Oct. Oct. Oct.
July Oct. Oct. Feb. Oct. 31, Feb. 3, Feb. 20, July 14, Feb. 28, Mar. 8,
Feb. 14, July 13, July 14, July 13, Oct. 31, Feb. 10, '64, Jan. 13, '64,
July 13, '63, Oct. 31, '61, Oct. 31, '61, July 13, '63, Jan. Oct. Oct.
Oct. Sept. Oct. Aug. Oct. Oct. Oct. Oct. Mar. Mar. Sept. Julv Oct. Mar.
Sept. July Oct. Sept. July Feb. Julv Feb. Oct. Oct. 13, '64, 31, '61,
31, '61, 31, '61, 16, '63, 13, '61, 1, '63, 31, '61, 31, '61, 31, '61, 31,
'61, 17, '64, 3, '64, 16, '63, 13, '63, 31, '61, 9, '64, 17, '62, 13, '63,
31, '61, 16, '63, 2r! '63 29', '64^ 15, '63, 24, 'G4, 13, '61, 13, '61,
Drafted— promoted to Corporal, Nov. 1, 1864— mustered out with
company, July 16, 1865. Promoted to Corporal, November 1, 1864—
mustered out with company, July 16, 1865. Drafted — promoted to
Corporal, Nov. 1, 1864 — mustered out with company, July 16. 1865.
Promoted to Corporal, November 1, 1864 — mustered out with
c;)mpany, July 16, 1865. Promoted to Corporal, .'inne 8, 1865 —
mustered out with company, July 16, 1865 — Vet. Promoted to
Corporal, .June 8, 1865— mustered out with company, .Tuly 16,
1865. INIustered out, Sept. 18, 1864— expiration of term. Mustered
out, Sept. 18, 1864— expiration of term. Mustered out, Sept. 18,
1864— expiration of term. Discharged on Surgeon's certificate, Oct.
10, '62. Discharged on Surgeon's certificate, Mar. 11, '63. Drafted—
discharged by Gen. Order, June 8, 1865. Killed at Antietam,
September 17, 1862. Deserted December 30, 1862. Prisoner from
May 28, 1864, to May 22, 1865— mustered out with company, July
16, 1865. Mustered out, Sept 18, 1864— expiration of term.
Mustered out with company, July 16, 1865. Transferred to Veteran
Kes.'Corps, Mar. 22, 1865. Drafted— discharged by Gen. Order, May
26, '65. jNIustered out with company, July 16, 1865. Mustered out
with company, July 16, 1865. Mustered out with company, July 16,
1865. Drafted— mustered out with Co., July 16, 1865. Drafted—
mustered out with Co., July 16, 1865. Drafted— mustered out with
Co., July 16, 1865. Drowned in Dam No. 6, Chesapeake and Ohio
Canal, February 9, 1862. Died Aug. 17, 1864, of wounds received at
Peach Tree Creek, Ga.— burial record, died at Chattanooga, Tenn.,
September 7, 1864 — grave, 657. Died of wounds received at
Bentonville, N. C, March 19, 1865— Vet. Drafted— died September
26, '63— buried at Alexandria, Va. — grave, 963. Died Aug. 19,
1862, (bu. record, Aug. 28, 1863,) of wounds received at Cedar
Mountain, Va., Aug. 9, '62— bu. at Alexandria, Va.— grave, 181.
Deserted December 30, 1862. Substitute— prisoner from Feb. 6, to
May 6, '65— mustered otat, July 16, 1865. Mustered out with
company, July 16, 1865— Vet. INIustered out, Sept. 18, 1864-
expiration of term. Discharged on Surgeon's certificate, Feb. 18, 63.
Discharged on Surgeon's certificate, Oct. 25, '62. Substitute—
discharged by G. O., May 30, 1865. Transferred to Vet. Res. Corps—
date unknown. Substitute— tr. to Vet. Res. Corps, Oct. 14, 1864.
Deserted August 17, 1862. Deserted August 17, 1862. Deserted June
30, 1862. Mis. in action at Cedar Mountain, Va., Aug. 9, '62. Not on
muster-out roll. Mustered out with company, July 16. 1865.
Substitute— mustered out with Co., July 16, '65. Drafted—
discharged by Gen. Order, May 22, '65. Transferred to Vet. Res.
Corps— date unknown. Killed at Peach Tree Creek, Ga., July 20,
1864Killed at Antietam, September 17, 1862. Drafted— mustered out
with Co., July 16, 1865. Discharo-ed on Surgeon's certificate, Dec. 9,
1862. Substitute— discharged by G. O., May 25, 1865. Substitute—
discharged bv G. O., April 27, 1865. Wounded at Dallas Gap, (5a.,
May 25, 1864— discharsied by General Order, May 17, 1865.
Drafte^l- died at Kelly's Ford, Va., Sept. 8, 1863. Died Julv 23, 1884,
of wds. rec. at Atlanta, Ga. Deserted January 25, 1863. Deserted
August 17, 1862.
 THREE YEARS' SERVICE. 1145 Gouldin, Martin. Goodrich,
Nathaniel Gloegle, Joseph., Graham, Paul F.. Grim, Daniel K ..,
Goughan, Martin.. Grier, James Houk, Franklin D, Hamaker, Patrick.
Harman, John C. Haberstick, Rud'h, Holloran, William.. Harrigan,
John Hearty, Patrick Hay, James Johnston, William J Johnson,
William... Koonts, George R... Kelley, James F. P Koonts, David
Kevlin, John Keener, .Jacob G.... Lehr, Edmund J... Lavery, John
Loudermilch, Jos... Lyter, Isaac Lanehan, John Leclere. Samuel A.
Lee, Edward Leonard, Michael .. Morton, William H Maughln, Martin
.. Murphy, Daniel , Metzger, John Malone, William... MiUan, John
Martin, Thomas.... Mullin, Patrick M'Laughlin, Owen M' Sweeney,
Dennis M'Lain, James A ... M'Gonegal, Peter... M'CuUough, Adam
M'Kennon, Thomas M'Tigert, Robert. Newton, Elijah J. Newton, John
H.. Newton, Charles.. Neill, William H... Oliver, James Ore, Patrick
Poits, Do,vid I Painter, Thomas.... Powell, Peter C Parham, William..
Phillipi, William... Private ..do ...do ...do, ...do. ...do, ...do. ...do.
...do. ...do. ...do. ...do. Rankin, Matthew T Reap, Patrick....
Shaddow, George W Singer, William Swartz, Martin. Stivison,
William.. Stuchall, Robert K Shriner, John Sweigard,George W
Sullivan, John..., Stewart, Robert.. 144 Jan. 12, '64, Mar. 7, '64, July
9, '63, July 14, '63, Sept. 16, '63, Oct. Oct. Jan. Feb. July Aug. Oct.
Oct. Oct. Mar. Oct. Jan. Dec. Mar. July 31, '61, 30, '61, 13, '63, 3,
'63, 31, '61, 31, '61, 31, '61, 8, '64, 31, '61, IS, '64, 12, '63, 3, '64,
23, '64, Mar. 24, Feb. 3, Feb. 1, Sept. 16, Mar. 16, Sept. 14, Oct. 31,
Sept. 16, July 14, Aug., Feb. 27, Jan. 13, April 12, '64, 3 Sept. 14,
*64, 1 July 14. '63, 3 Oct. 31, '61, 3 Oct. 31, '61, 8 Oct, 31, '61, 3
Mar. 31, '64, 3 July 13, '6.3, 3 Sept. 13, '63, 3 Oct. 31, '61, 3 Julv 11,
'63, 3 Feb. 24, '64, 3 Oct. 13, '61, 3 Jan. 4, '64, 3 J.nn. 4, '64, 3 Mar.
9, '64, 3 July 13, '63, 3 Oct. 13. '61, 3 Oct. 13, '61, 3 July 14, '63, 3
July 13, '63, 3 Oct. 31, '61, 3 Oct. 31, '61, 3 July 16, '63, 3 July 13,
'63, 3 Jan. 13, '64, 3 Mar. 4, '64, 3 Feb. 20, '64, 3 Mar. «, '64, 3 July
13, '63, 3 July 13, '63, 3 Feb. 10, '64, 3 Feb. 22, '64. 3 Oct. 31, '61,
3 July 13, '63,, 3. Mustered out with company, July 16, 1865— Vet.
Mustered out with company, July 16, 1865. Drafted— wounded at
Peach Tree Creek, Ga., July 20, 1864— absent, in hospital, at muster
out. Drafted— disch. on Surgeon's cert., Jan. 8, 1864. Drafted—
deserted November 19, 1864— returned May 10, 1865— discharged
May 11, 1865. Discharged on Surgeon's certificate, Aug. 16, '62.
Deserted June 9, 1862. Mustered out with company, July 16, 1865.
Mustered out with company, July 16, 1865. Drafted— mustered out
with Co., July 16, 1865. Substitute — mustered out with Co., July 16,
'65. Discharp:ed on Surgeon's certificate, Feb. 25, '63. Discharged on
Surgeon's certificate. Mar. 15, '63. Discharged on Surgeon's
certificate, Dec. 9, '62. Deserted July 1, 18'65. Discharged on
Surgeon's certificate. Mar. 31, '63. Deserted February' 9, 1865— Vet.
Mustered out with company, July 15, 1865. Mustered out with
company, July 15, 1865. Substitute— wounded in action. May 15,
1864— absent, in hospital, at muster out. Discharged by iSeneral
Order, July 10, 1865. Deserted June 23. 1865. Mustered out with
company, July 16, 1865. Drafted— mustered out with Co., July 16,
1865. Absent, sick, at muster out. Discharged by General Order,
June 8, 1865. Exec'dfor the murder of Maj. Lewis, Dec. 23, '61.
Drafted — died at Savannah, Ga., June 22, 1865. Substitute —
deserted September 30, 1864. Not mustered into United States
service. Mustered out with company, July 16, 1865. Pris.fr. Aug. 9, to
Sept. 13,'62,andfr.May2,toMay 15, 186.3— mus. out with Co., July
16, 1865— Vet. Wounded, in action, July 20, 1864— absent, in
hospital, at muster out. Discharged by General Order, June 8, 1865.
Substitute— died at Goldsboro', N. C.,Mar. 27,'65. Deserted
Deoember 30, 1862. Deserted Ausrust 11, 1862. Deserted January
19, 1862. Mustered out with company, July 16, 1865 — Vet. Drafted
— mustered out with Co., 'July 16, 1865. Drafted — disch. by
General Order, June 5, 1865. Discharged on Surgeon's certificate,
Oct. 16, '62. Drafted^disch. on Surgeon's cert., Feb. 13, 1864.
Deserted May 13, 1864. Not on muster-out roll. Mustered out with
company, July 16, 1865. Mustered out with company, July 16, 1865.
Prisoner from March 3, to March 30, 1865— discharged bv General
Order, June 29, 1865. Drafted— disch. by General Order, June 21,
1865. Deserted Julv 1, 1862. Deserted December 30, 1862. Drafted
— mustered out with Co., July 16, 1865. Drafted— mustered out
with Co., July 16, 1865. Mustered out, Sept. 18, 1864 — expiration
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