Silicon-containing carbanions. I. Synthesis of vinyl thio ethers and vinylphosphonates via silicon-modified organolithium reagents

FA Carey, AS Court

Index: Carey,F.A.; Court,A.S. Journal of Organic Chemistry, 1972 , vol. 37, p. 939 - 943

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Citation Number: 38

Abstract

Reactions of diethyl 1-lithio-1-trimethylsilylmethylphosphonate (1) and l-trimethylsilyl-l- phenylthiomethyl-lithium (2) with representative aldehydes and ketones are reported which provide useful routes to diethyl vinylphosphonates (6a-g) and vinyl phenylthioethers (18a-g) by loss of MerSiOLi from the presumed intermediate resulting from attack of the organolithium reagent at the carbonyl group. It was found that the exocyclic ...