Issue 0, 1981
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Reaction of epoxides with triphenylphosphine–thiocyanogen (TPPT): preparation of α-thiocyanatovinyl ketones, vic-dithiocyanates, and vic-dithiocyanatohydrins

Yasumitsu Tamura,   Tomomi Kawasaki,   Hitoshi Yasuda,   Noriko Gohda  and  Yasuyuki Kita  

Abstract

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-dithio-cyanate 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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Article information

DOI
https://doi.org/10.1039/P19810001577
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 1577-1581

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Reaction of epoxides with triphenylphosphine–thiocyanogen (TPPT): preparation of α-thiocyanatovinyl ketones, vic-dithiocyanates, and vic-dithiocyanatohydrins

Y. Tamura, T. Kawasaki, H. Yasuda, N. Gohda and Y. Kita, J. Chem. Soc., Perkin Trans. 1, 1981, 1577 DOI: 10.1039/P19810001577

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