Dimsyl anion with carboxylic esters

TABLE 25. Reaction of dimsyl anion with carboxylic esters... 

The first reports on this reaction were published almost simultaneously by Russell and coworkers533 and Corey and Chaykovsky534, who reacted dimsyl anion with a variety of carboxylic esters and obtained the corresponding a-ketosulphoxides 464 in high yields (equation 277 Table 25). 

Dimsyl anion 88 reacts with esters of aromatic carboxylic acids and aliphatic acids which do not have a readily transferable proton, to give /5-ketosulfoxides114,133,138-141. There are not many cases in which acyl chlorides were used142,143. However, the reaction... 

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