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Oppenauer Oxidation

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Bibi Khadiza
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47 views20 pages

Oppenauer Oxidation

Uploaded by

Bibi Khadiza
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
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Group -06

Oppenauer
Oxidation
Group Members
• Nourin Khan Chowdhury
(22346054)
• Tahsin Uddin Jisan (22346056)
• Bibi Khadiza (22346057)
• Rahnuma Nurain Tanha
(22346059)
• Md. Arafat Rahman (22346061)
What is the Oppenauer
Oxidation Process?
A gentle method for selectively oxidizing secondary alcohols to ketone
aldehydes using aluminum isopropoxide as a catalyst, typically in the
presence of acetone as an oxidizing agent. This method is especially
useful for converting secondary alcohols to ketones while minimizing
over-oxidation.
Story Behind
Discovery
• In the early 20th century, organic chemists were focused on finding mild,
selective methods to oxidize specific alcohols without damaging other
sensitive parts of complex molecules.

• Oppenauer was inspired by Meerwein–Ponndorf–Verley (MPV) reduction.

• In 1937, Oppenauer successfully demonstrated by using aluminum


isopropoxide as a catalyst and acetone as an oxidizing agent
The Reactants and
• Secondary Alcohol
Products • Aluminium Alkoxide
(typically aluminum
isopropoxide)

• Ketone • Overall
(usually acetone) Transformation:

Secondary alcohol + Ketone


(acetone) → Ketone (product) +
Secondary alcohol (isopropanol)
Mechanism of Action
Step-01: Complex
Formation
Step 02:
Hydride Transfer & Ketone Formation
Step 03:
Isopropyl Alcohol Formation
Why “Secondary Alcohols”
Only?
Critical Insights on
Stereochemistry
Synthesis of Progesterone
“Retention of Configuration”
Advantages of Oppenauer
Oxidation Selective
Oxidation
Catalyst
Recyclability
Compatibility with
Sensitive
Substrates

Minimal Over
Mild reaction Regioselectivity
Oxidation
conditions
Limitations of Oppenauer
Oxidation Lower
Substrate
limitation yields
Over-oxidation
Regioselectivity risk
issues Solvent
reactivity
Steric Harsh
Hindarance conditions
Applications of Oppenauer
OxidationSteroid and
Hormone
Synthesis of Ketone- Modification
Based
Drugs Green Chemistry
Applications
Synthesis of Natural
Product Manufacture of
Derivatives Intermediates
for Complex Organic
Molecules
References
• Yang, S. (2021, April 26). Oppenauer Oxidation. J&K Scientific LLC.
https://www.jk-sci.com/blogs/resource-center/oppenauer-oxidation?srsltid=AfmBOoqnnmNRM9sM8kM78L
bl0aCVrZNl7XsJvPmrKzdJRaPgHwYt-u7O
• C. J. S. A. Kumar, D. M. M. (2015). "Recent developments in Oppenauer oxidation of alcohols: Mechanisms
and applications." Tetrahedron, 71(11), 1767-1786 DOI: 10.1016/j.tet.2015.02.021
• https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=11ad4fe8bb3644159a0e452a11212c
b5bd322706
• https://pubs.acs.org/doi/abs/10.1021/jo001750u
• Morrison, R. T., & Boyd, R. N., Organic chemistry, Allyn and Bacon, Inc. 1987
• Skyes, P., A Guide Book to Mechanism in Organic Chemistry, Second edition, Orient Longman Ltd., 1988
• March, J., Advanced Organic Chemistry, Wiley Eastern Limited, 1986.
• https://ebrary.net/193190/health/chiral_pharmaceuticals_source_human_risk_future_studies?
form=MG0AV3
• https://www.maxbrainchemistry.com/p/synthesis-of-progesterone.html?form=MG0AV3
Any
Questions?

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