1663-62-3Relevant academic research and scientific papers
VINYL ETHERS CONTAINING AN EPOXY GROUP. FEATURES OF THE REACTION OF GLYCIDOL VINYLOXYETHYL ETHER WITH THIOLS
Nedolya, N. A.,Komel'kova, V. I.,Al'pert, M. L.,Trofimov, B. A.
, p. 424 - 430 (2007/10/02)
The reaction of thiols with glycidol vinyloxyethyl ether under radical and electrophilic conditions, leading to adducts at the vinyloxy group, was investigated.The reaction in the presence of perfluorobutyric and p-toluenesulfonic acids gives a mixture of "Markovnikov" and "anti-Markovnikov" addition products with a preference for the latter.Nine representations of the class of epoxy sulfides and their adducts with alcohol, thiols, amines, and urea were synthesized and characterized.It was found that the radical addition of the thiols to the vinyloxy group is accelerated in the presence of acids.This was explained by single-electron transfer between the thioanion and the carbenium ion.
