Bulletin of the Chemical Society of Japan p. 3957 - 3964 (1988)
Update date:2022-07-30
Topics:
Kanemasa, Shuji
Kobayashi, Hiroshi
Tanaka, Junji
Tsuge, Otohiko
Reaction of organolithiums with a 1-(trimethylsilyl)ethenyl sulfide produces 1,2-bis(trimethylsilyl)-cyclopropanes, while use of 1-silylethenyl sulfides bearing a bulkier silyl moiety results in exclusive formation of the corresponding Michael adducts anions which are then quenched with aldehydes to give vinyl sulfides.On the contrary, a 1-(trimethylsilyl)ethenyl sulfoxide undergoes smooth Michael addition with a variety of organometallics and the resulting carbanion intermediates can be quenched with aldehydes to produce vinyl sulfoxides.Scope and limitations of these sequential reactions are discussed.
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(1988)
