78508-38-0Relevant academic research and scientific papers
Reaction of Epoxides with Triphenylphosphine-Thiocyanogen (TPPT): Preparation of α-Thiocyanatovinyl Ketones, vis-Dithiocyanates, and vic-Dithiocyanatohydrins
Tamura, Yasumitsu,Kawasaki, Tomomi,Yasuda, Hitoshi,Gohda, Noriko,Kita, Yasuyuki
, p. 1577 - 1581 (1981)
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.
PSEUDOHALOGEN CHEMISTRY-X STERIC EFFECTS IN THE HOMOLYTIC ADDITION OF THIOCYANOGEN TO ALKENES
Guy, Robert G.,Thompson, Jeffrey J.,White, Trevor J.
, p. 33 - 38 (2007/10/02)
Homolytic addition of thiocyanogen to alkenes with at least three methyl groups or two phenyl groups on the double bond gives vicinal dithiocyanates and/or thiocyanaao-isothiocyanates.The addition to (E)- and (Z)- PhCH=CHPh is in non-stereospecific, but the thiocyanato-isothiocyanates derived from unsymmetrical alkenes are formed regiospecigically with the isothiocyanato group being attached to the more heavily substituted C atom.A radical-chain mechanism, involving competing kinetically-controlled chain transfer at the S atom and sterically-controlled chain transfer at the N atom of the thiocyanogen molecule, is propodes.Keywords: Steric effects; homolytic addition; thiocyanogen; alkenes
