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.
TY - JOUR
AU - Džambaski, Zdravko
AU - Toljic, Dorde
AU - Bondžić, Bojan
AU - Marković, Rade
AU - Baranac-Stojanović, Marija
PY - 2013
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/1263
AB - 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.
PB - Pergamon-Elsevier Science Ltd, Oxford
T2 - Tetrahedron
T1 - Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions
VL - 69
IS - 46
SP - 9819
EP - 9825
DO - 10.1016/j.tet.2013.09.004
ER -
@article{
author = "Džambaski, Zdravko and Toljic, Dorde and Bondžić, Bojan and Marković, Rade and Baranac-Stojanović, Marija",
year = "2013",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/1263",
abstract = "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.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions",
volume = "69",
number = "46",
pages = "9819-9825",
doi = "10.1016/j.tet.2013.09.004"
}
Džambaski, Z., Toljic, D., Bondžić, B., Marković, R.,& Baranac-Stojanović, M. (2013). Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions.
Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 69(46), 9819-9825.
https://doi.org/10.1016/j.tet.2013.09.004
Džambaski Z, Toljic D, Bondžić B, Marković R, Baranac-Stojanović M. Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions. Tetrahedron. 2013;69(46):9819-9825
Džambaski Zdravko, Toljic Dorde, Bondžić Bojan, Marković Rade, Baranac-Stojanović Marija, "Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions" Tetrahedron, 69, no. 46 (2013):9819-9825,
https://doi.org/10.1016/j.tet.2013.09.004 .
