76014-52-3Relevant academic research and scientific papers
PSEUDOHALOGEN CHEMISTRY-VII. ADDITION OF THIOCYANOGEN TO ALKYNES
Guy, R. G.,Cousins, S.,Farmer, D. M.,Henderson, A. D.,Wilson, C. L.
, p. 1839 - 1842 (1980)
Thiocyanogen does not react with simple alkynes under heterolytic conditions in benzene at 20-25 deg C.Under homolytic conditions, addition occurs readily giving mixtures of E- and Z-dithiocyanatoalkenes with high E:Z ratios; prolonged treatment with excess reagent also leads to mixtures of the dithiocyanatoalkenes but usually with lower E:Z ratios.A radical-chain mechanism, involving preferential anti-addition of thiocyanogen in an initial kinetically-controlled reaction and subsequent thermodynamically-controlled isomerisation of the adducts, is proposed.The influence of substituents on the reaction rates and product ratios is discussed in terms of their steric effects.
