Tetrahedron

Reaction of diazomethane with selenoesters: Preparation of α-(alkyl-or arylseleno) methyl ketones and methyl ketones

TG Back, RG Kerr

Index: Back, Thomas G.; Kerr, Russell G. Tetrahedron, 1985 , vol. 41, # 21 p. 4759 - 4764

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Citation Number: 27

Abstract

The reaction of diazomethane with a series of selenoesters 1 in the presence of CuI, CuSePh or Cu powder produced α-(alkyl-or arylseleno) methyl ketones 2 in yields of 41– 65%. Methyl ketones 3 and bis (arylseleno) methanes 9 or 14 were formed as by-products. The direct conversion of selenoesters to methyl ketones was accomplished in high yield by the usual reaction with diazomethane, followed by workup with HBr solution. The ...