Journal of Organic Chemistry p. 844 - 849 (1987)
Update date:2022-08-04
Topics:
Katritzky, Alan R.
Kuzmierkiewicz, Wojciech
Aurrecoechea, Jose M.
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.
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