Comparison of tris(dimethylphenylsilyl)methyllithium and tris(trimethylsilyl)methyllithium reactions with carbon disulfide: a new route for the synthesis of some 1,1-bis(benzylthio)- and bis(allylthio)-2,2-bis(dimethylphenylsilyl)ethenes

Abstract

A series of bis(benzylthio)- and bis(allylthio)-2,2-bis(dimethylphenylsilyl) ethenes has been obtained by the reaction of (PhMe₂Si)₃CLi and CS₂ with benzyl and allyl bromides. A plausible mechanism for the formation of these compounds has been proposed. The reactivity of (PhMe₂Si)₃CLi toward CS₂ has been compared with that of (Me₃Si)₃CLi. The reaction of (PhMe₂Si)₃CLi with CS₂ and 2-methyloxirane gave a cyclic thiocarbonate.

GRAPHICAL ABSTRACT

• organosilicon-sulfur
• mercaptobis-(trimethylsilyl)-thione
• tris(dimethylphenylsilyl)methyllithium
• tris(trimethylsilyl)methyllithium
• carbon disulfide

Acknowledgement

We thank Dr J. D. Smith for helpful comments.