Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions
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The reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions, using Ac2O, TFAA, SOCl2 and SOBr2 as initiators, has been examined. Almost all reactions proceeded with absolute regioselectivity yielding alpha-substituted sulfides or vinyl-chloro derivatives. The mechanism for the formation of the latter products was postulated and proved experimentally. (C) 2013 Elsevier Ltd. All rights reserved.
Keywords:Pummerer reaction / 2-Alkylidene-4-oxothiazolidine S-oxide / Regioselectivity / Density functional calculations
Source:Tetrahedron, 2013, 69, 46, 9819-9825
- Pergamon-Elsevier Science Ltd, Oxford