Bayer-Villiger Oxidation in Organic Synthesis

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

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.