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Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions

Authorized Users Only
2013
Authors
Džambaski, Zdravko
Toljic, Dorde
Bondžić, Bojan
Marković, Rade
Baranac-Stojanović, Marija
Article (Published version)
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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.
Keywords:
Pummerer reaction / 2-Alkylidene-4-oxothiazolidine S-oxide / Regioselectivity / Density functional calculations
Source:
Tetrahedron, 2013, 69, 46, 9819-9825
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)

DOI: 10.1016/j.tet.2013.09.004

ISSN: 0040-4020

WoS: 000326768800035

Scopus: 2-s2.0-84885181662
[ Google Scholar ]
4
4
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1263
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Toljic, Dorde
AU  - Bondžić, Bojan
AU  - Marković, Rade
AU  - Baranac-Stojanović, Marija
PY  - 2013
UR  - https://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  - Oxford : Pergamon-Elsevier Science Ltd
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",
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 = "Oxford : Pergamon-Elsevier Science Ltd",
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. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 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. in Tetrahedron. 2013;69(46):9819-9825.
doi:10.1016/j.tet.2013.09.004 .
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" in Tetrahedron, 69, no. 46 (2013):9819-9825,
https://doi.org/10.1016/j.tet.2013.09.004 . .

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