Behaviors of. ALPHA.-Fluorocarbenoids Derived from the Nucleophilic Desulfinylation of. ALPHA.-Chloro-. ALPHA.-fluoroalkyl Sulfoxides.

H Uno, K Sakamoto, F Semba, H Suzuki

Index: Uno, Hidemitsu; Sakamoto, Katsuji; Semba, Fumihiko; Suzuki, Hitomi Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 1 p. 210 - 217

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Citation Number: 47

Abstract

2-Aryl-1-chloro-1-fluoroethyl sulfoxides underwent nucleophilic desulfinylation with PhMgBr to give (Z)-fluorostyrene derivatives in a very stereoselective manner (> 33: 1) via an α- fluorocarbene species. When treated with 3 equiv of PhLi in the presence of N, N, N′, N′- tetramethylethylenediamine, they similarly formed fluorostyrenes as a stereoisomeric mixture (E: Z= 2: 1), but with 1 equiv of PhLi 2-aryl-1-chloro-1-fluoroethanes were the ...