The oxidative conversion of alicyclic ketones into lactones with permonosulfuric acid was discovered by Baeyer and Villiger in 1899, and in their honor the general process by which ketones are converted into esters or lactones is now known as the Baeyer–Villiger reaction. The literature on this synthetically useful process has been reviewed comprehensively through 1953 in Volume 9 of Organic Reactions, and less comprehensive reviews of the reaction have appeared since then. More recent investigations have led to the development of new synthetic reagents, to improvements in experimental reaction conditions, and to a better understanding of regiochemical and stereochemical aspects of the reaction. Baeyer–Villiger reactions now often can be carried out with functional group chemoselectivity and regiochemical control. Although the recent removal from commerce of 90% hydrogen peroxide and reagents based upon this oxidant are a setback to Baeyer–Villiger reaction methodology, alternative reagents, catalysts, and methods described in this review are available to fill the gaps.



The definition of the Baeyer–Villiger reaction is somewhat fuzzy, and can be considered to include both ketones and aldehydes. In addition to the traditional use of organic and inorganic peracids as oxidants, examples of oxygen insertion reactions using hydrogen peroxide, alkyl peroxides, and several metal ion oxidants are considered to fall within the scope of this chapter and are included in the tabular survey.


Keywords:

Baeyer-Villiger oxidation;
ketones;
aldehydes;
Criegee mechanism;
migrating step;
rate determining addition;
straight chain ketones;
monocyclic ketones;
polycyclic ketones;
α,β-unsaturated ketones;
1,2 dicarbonyls;
reagents;
fused ring ketones;
peracid reactions;
α,β-unsaturated aldehydes;
ketals;
acetals;
side reactions;
alternative methods;
experimental procedures;
scope;
limitations;
spirocyclic ketones;
bridged compounds;
nitrogen derivatives

The Baeyer–Villiger Oxidation of Ketones and Aldehydes

Criegee rearrangement of α-alkoxy hydroperoxides a synthesis of esters and lactones that complements the baeyer-villiger oxidation of ketones

Isomeric structures of protonated carbon dioxide

Rearrangements of Carbocations

Die Methanolyse des trans-Decalyl-(4a)-phenylperacetats erfolgt heterolytisch nach dem Criegee-Mechanismus4), die Thermolyse in Athylbenzol durch homolytische Fragmentierung4). Die Konkurrenz der beiden Zerfallswege wird durch das Solvens und Substituenten im Persaureester stark beeinflust. Kriterien zum Nachweis konkurrierender homolytischer und heterolytischer Zerfallsweisen von Perestern wurden untersucht.

Organische Peroxide, VIII. Thermolyse und Solvolyse substituierter trans‐Decalyl‐(4a)‐phenylperacetate

The Ionic Decomposition of 2-Substituted 2-Propyl p-Nitroperbenzoates. Migration to Electron-Deficient Oxygen and Anchimeric Acceleration of Peroxide-Bond Heterolysis

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The Ionic Decomposition of 2-Substituted 2-Propyl p-Nitroperbenzoates. Migration to Electron-Deficient Oxygen and Anchimeric Acceleration of Peroxide-Bond Heterolysis