Tetrahedron

Synthesis of mono-and disubstituted sulfines via β-elimination of chloroform from trichloromethyl sulfoxides

S Braverman, D Grinstein, HE Gottlieb

Index: Braverman, Samuel; Grinstein, Dan; Gottlieb, Hugo E. Tetrahedron, 1997 , vol. 53, # 40 p. 13933 - 13944

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Citation Number: 15

Abstract

A new method for the synthesis of thioaldehyde and thioketone S-oxides by an unusual base-induced β-elimination of chloroform from readily available allylic and benzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. The facile preparation of α, β-unsaturated sulfines by the new method is of special interest. A possible mechanism for this remarkable sulfine synthesis and ...