Bayer-Villiger Oxidation in Organic Synthesis

Study Notes

Bayer-Villiger Oxidation in Organic Synthesis

What is Bayer-Villiger Oxidation?

A type of organic reaction used to convert ketones into esters
Involves the oxidation of a ketone to form an ester via a peroxide intermediate

Mechanism

The reaction involves the formation of a Criegee intermediate, which then rearranges to form the ester
The mechanism involves a concerted, asynchronous process

Reaction Conditions

Typically performed using a peracid (e.g. m-CPBA) as the oxidizing agent
Reaction conditions: mild temperatures, neutral to acidic pH, and often in the presence of a catalyst

Scope and Applicability

Useful for the synthesis of complex molecules, including natural products and pharmaceuticals
Can be used to introduce oxygen functionality into molecules
Often used in conjunction with other reactions to form complex molecular architectures

Advantages and Limitations

Advantages: mild reaction conditions, high yields, and tolerance of various functional groups
Limitations: can be sensitive to steric and electronic factors, and may require optimization of reaction conditions

Examples and Applications

Used in the synthesis of various natural products, including steroids and terpenes
Applied in the production of pharmaceuticals, such as antibiotics and anti-inflammatory agents

Description

Test your knowledge of the Bayer-Villiger oxidation reaction, a useful tool in organic synthesis for converting ketones into esters. Learn about the mechanism, reaction conditions, scope, and applications of this important reaction.