Villiger, Victor

The reaction of ketones with peroxy acids is both novel and synthetically useful An oxygen from the peroxy acid is inserted between the carbonyl group and one of the attached car bons of the ketone to give an ester Reactions of this type were first described by Adolf von Baeyer and Victor Vilhger m 1899 and are known as Baeyer—Villiger oxidations... 

The Baeyer-Villiger oxidation reaction was discovered more than 100 years ago by Adolf von Baeyer and Victor Villiger. By this reaction, ketones are converted into the corresponding esters. In organic chemistry, peracids are commonly used as catalyst to perform this atypical oxidation reaction that results in oxygen insertion into a carbon—carbon bond (Fig. 1). 

Baeyer-Villiger ReactionJ Adolf von Baeyer (Nobel Prize, 1905) in collaboration with Victor Villiger showed that treatment of cyclic ketones with monoperoxysulfuric acid (HO2SO3H) produced lactones. The great synthetic utility of the reaction is derived from its stereospecificity and often high degree of regioselectivity. Moreover, the reaction proceeds under mild conditions and can be applied to acyclic, cyclic, and aromatic ketones. 

Although Chapter 17 discussed several oxidation reactions, an important reaction was not discussed in that chapter. Section 17.3 discussed the oxidation of an alkene to an epoxide using a peroxyacid such as 163 (also see Chapter 10, Section 10.5). Peroxyacids also react with ketones to form esters in what is known as the Baeyer-Villiger reaction. This reaction is named in honor of its discoverers, Johann Friedrich Wilhelm Adolf von Baeyer (Germany 1835-1917) and Victor Villiger (Switzerland 1868-1934). 

Johann Friedrich Wilhelm Adolf von Baeyer (1835-1917) studied under Bunson and Kekuld at the University of Heidelberg and Hofmann at the University of Berlin (from which he received the doctorate). Victor Villiger was von Baeyer s student. As an interesting footnote, although this work was first published in 1899, it received little attention presumably because suitable peracids were not widely available. Baeyer, A. Villiger, V. Chem. Ber., 1899, 32, 3625. A review has appeared see Krow, G. R. Org. React.,1992., 43,25Ut... 

This reaction, discovered by Adolf von Baeyer and Victor ViUiger in 1899, is called the Baeyer-Villiger oxidation. This process is beUeved to proceed via Mechanism 20.13. 

Professor Johann Friedrich Wilhelm Adolf von Baeyer (1835-1917), University of Munich, Nobel Prize 1905 (chemistry) Victor Villiger (1868-1934), BASF, Ludwigshafen, Germany. 

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