Tetrahedron

New method for generation of β-oxido carbenoid via ligand exchange reaction of sulfoxides: A versatile procedure for one-carbon homologation of carbonyl …

T Satoh, N Itoh, K Gengyo, S Takada, N Asakawa…

Index: Satoh, Tsuyoshi; Itoh, Norifumi; Gengyo, Kaoru; Takada, Sae; Asakawa, Naoyuki; et al. Tetrahedron, 1994 , vol. 50, # 41 p. 11839 - 11852

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Citation Number: 33

Abstract

A new procedure for one-carbon homologation of carbonyl compounds is described. The method is based on the rearrangement of β-oxido carbenoid which is generated via the ligand exchange reaction of the sulfinyl group of α-chloro β-hydroxy sulfoxide with tert- butyllithium. Addition of the carbanion of aryl 1-chloroalkyl sulfoxides to carbonyl compounds gave the adducts in good yields. The β-oxido carbenoid rearrangement of the ...

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