Journal of the Chemical Society. Perkin transactions I p. 1577 - 1581 (1981)
Update date:2022-08-04
Topics:
Tamura, Yasumitsu
Kawasaki, Tomomi
Yasuda, Hitoshi
Gohda, Noriko
Kita, Yasuyuki
A number of epoxides smoothly react with TPPT under mild conditions to give α-thiocyanatovinyl ketones, vic-dithiocyanates, or vic-thiocyanatohydrins, depending on the structures of the epoxides used.The reactions proceed site- and stereo-specifically, to give α-thiocyanatovinyl ketones from αβ-epoxyketones, threo-dithiocyanate from trans-epoxide, erythro-dithiocyanate from cis-epoxide, and vic-thiocyanatohydrins from 1,1-disubstituted or fused epoxides, respectively.A possible mechanism for these reactions is put forward.
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Doi:10.1007/BF00949722
(1981)Doi:10.1016/S0040-4039(00)74720-4
(1992)Doi:10.1021/jo00156a018
(1983)Doi:10.1016/S0040-4020(01)88450-7
(1984)Doi:10.1016/j.steroids.2005.04.008
(2005)Doi:10.1021/jo005602f
(2000)
