- Reaction of Epoxides with Triphenylphosphine-Thiocyanogen (TPPT): Preparation of α-Thiocyanatovinyl Ketones, vis-Dithiocyanates, and vic-Dithiocyanatohydrins
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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.
- Tamura, Yasumitsu,Kawasaki, Tomomi,Yasuda, Hitoshi,Gohda, Noriko,Kita, Yasuyuki
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p. 1577 - 1581
(2007/10/02)
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