112929-68-7Relevant academic research and scientific papers
The rates and products of addition of 4-chlorobenzenesulfenyl chloride to a series of trisubstituted alkenes
Schmid, George H.,Garratt, Dennis G.,Dean, Coleen L.
, p. 1172 - 1176 (2007/10/02)
The rates and products of addition of 4-chlorobenzenesulphenyl chloride to E- and Z-3-methyl-2-pentene, E- and Z-3,4-dimethyl-2-pentene, E- and Z-3,4,4-trimethyl-2-pentene, and 2,4,4-trimethyl-2-pentene were studied to determine if the mechanism involved a tertiary β arylthio carbocation.It was found that the rates of addition are not as fast as one would predict based on the polar effects of the substituents on the rate of addition to mono- and disubstituted alkenes.The products are formed by anti-stereospecific addition as in the case of addition to 1,2-disubstituted alkenes.As a result it is concluded that the reaction occurs by means of the usual mechanism involving a bridged thiiranium ion.
