Reaction of bulky organosilicon compounds with CS2: Cleavage and rearrangement reactions of 1,2-epoxides

The reaction of tris(trimethylsilyl)methyllithium, (Me3Si)3CLi, and carbon disulfide with various epoxides have been studied. By an unusual rearrangement hydroxy-mercaptobis-(trimethylsilyl)-thiones have been synthesized in good yields. Unexpectedly, in the case of 2-phenyloxirane two structural isomers (2g) and (2h) have been formed which was confirmed by IR, 1H and 13C NMR spectroscopy. Moreover, the reaction of (PhMe2Si)3CLi and (Me3Si)3CLi with CS2 in the presence of epoxides has been compared.