The Use of tert-Butyl Vinyl Ether in Stepwise Electrophilic Addition Reactions

LN Koikov, M Han, DM Wellman, JA Kelly…

Index: Koikov, Leonid N.; Han, Mingming; Wellman, Dawn M.; Kelly, Jim A.; Smoliakova, Irina P. Synthetic Communications, 2000 , vol. 30, # 18 p. 3451 - 3464

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Citation Number: 5

Abstract

Abstract tert-Butyl vinyl ether (1) reacts with p-TolSCl to give 2-tert-butoxy-2-chloroethyl p- tolyl sulfide (2). In the presence of SnCl4, 2 reacts with silyl enol ethers, allyltrimethylsilane, and vinyl ethers to form a CC bond. In the case of vinyl ethers, the reaction proceeds through the formation of the 5-membered sulfonium salt intermediate which in turn can react with H2O, TMSCN, allyltrimethylsilane, and Grignard reagents.