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

• The treatment of (Me3Si)3CLi and CS2 with epoxides yielded new compounds.
• These compounds were named as hydroxyl-mercaptobis-(trimethylsilyl)-thiones.
• The reaction of (PhMe3Si)3CLi and CS2 with 2-methyloxiran gave cyclic thiocarbonate.

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.

The treatment of (Me3Si)3CLi and CS2 with some epoxides has been yielded novel multifunctional compounds. We named these compounds as hydroxyl-mercaptobis-(trimethylsilyl)-thiones. The reaction of (PhMe3Si)3CLi and CS2 with 2-methyloxiran gave cyclic thiocarbonate.Figure optionsDownload as PowerPoint slide