Recently, an isolable diakylsilylene 1  as starting materials for the synthesis of new type interesting compounds has been reported1. Its remarkable reactivity towards numerous unsaturated organic and organometallic substrates prompted us to investigate the behavior of silylene 1  with various substituted of imines. Reactions of an isolable dialkylsilylene1  with imines occur in solution to afford the silaaziridines and azasilacyclobutane according to imines used. For example, aldimines 2a -c  reacted with 1  smoothly to afford silaaziridines 3 ,  4 , and azasilacyclobutane 5  in good yields respectively without formation of any secondary or side-reaction products. Under similar conditions, however, the silane 6  was obtained from imine 2d  in moderate yield. The reaction mechanism of dialkylsilylene1  with imines will be discussed.All products are very stable, which have been fully characterized by 1H, 13C, and 29Si NMR spectroscopy, MS, and single-crystal X-ray diffraction.

Silaaziridine from the reaction of didalkylsilylene with imine

243rd National Meeting (2012)

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