Tetrahedron p. 1839 - 1842 (1980)
Update date:2022-09-26
Topics:
Guy, R. G.
Cousins, S.
Farmer, D. M.
Henderson, A. D.
Wilson, C. L.
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.
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Doi:10.1021/jo01278a059
(1967)Doi:10.1016/j.bmcl.2013.06.046
(2013)Doi:10.1016/S0022-1139(00)85218-5
(1980)Doi:10.1021/jo00142a025
(1982)Doi:10.1021/jm0311285
(2004)Doi:10.1016/S0008-6215(00)85907-8
(1980)
