Reactions of (benzothiazol-2-ylthio)(trimethylsilyl) methane. A general method for. alpha.-mercaptoalkylation by alkylation and alkylative desilylation

…, W Kuzmierkiewicz, JM Aurrecoechea

Index: Katritzky, Alan R.; Kuzmierkiewicz, Wojciech; Aurrecoechea, Jose M. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 5  p. 844 - 849

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Citation Number: 16

Abstract

Readily available (benzothiazol-2-ylthio)(trimethylsilyl) methane (2a) provides a convenient synthon for HSCH2-and enables the general conversions RR'CO-RR'C (OH) CH (SH) R” and RBr-RCH (SH) SiMe3 The lithium derivative of 2a reacts with aldehydes and ketones to give Peterson olefination products which are protected vinyl mercaptans converted into vinyl mercaptans by reaction with methyllithium. This overall conversion is RR'CO-RR'C: CHSH.