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Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles

Authorized Users Only
2010
Authors
Baranac-Stojanović, Marija
Tatar, Jovana
Stojanović, Milovan
Marković, Rade
Article (Published version)
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Abstract
Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph(3)P, AcS(-), CN(-), I(-), F(-), Ac(2)CH(-) and N(3)(-) the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et(3)N or morpholine, are employed as nucleophiles the initial bromophilic attack is followed by bromine migration to the C(5) position of the ring, allowing the C(5) functionalization of this heterocyclic system.
Keywords:
4-Oxothiazolidine / Vinyl bromide / Bromophilic reaction / Carbanion / Rearrangement
Source:
Tetrahedron, 2010, 66, 34, 6873-6884
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-142007)

DOI: 10.1016/j.tet.2010.06.057

ISSN: 0040-4020

WoS: 000280953500026

Scopus: 2-s2.0-77955469036
[ Google Scholar ]
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/700
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Tatar, Jovana
AU  - Stojanović, Milovan
AU  - Marković, Rade
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/700
AB  - Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph(3)P, AcS(-), CN(-), I(-), F(-), Ac(2)CH(-) and N(3)(-) the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et(3)N or morpholine, are employed as nucleophiles the initial bromophilic attack is followed by bromine migration to the C(5) position of the ring, allowing the C(5) functionalization of this heterocyclic system.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles
VL  - 66
IS  - 34
SP  - 6873
EP  - 6884
DO  - 10.1016/j.tet.2010.06.057
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Tatar, Jovana and Stojanović, Milovan and Marković, Rade",
year = "2010",
abstract = "Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph(3)P, AcS(-), CN(-), I(-), F(-), Ac(2)CH(-) and N(3)(-) the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et(3)N or morpholine, are employed as nucleophiles the initial bromophilic attack is followed by bromine migration to the C(5) position of the ring, allowing the C(5) functionalization of this heterocyclic system.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles",
volume = "66",
number = "34",
pages = "6873-6884",
doi = "10.1016/j.tet.2010.06.057"
}
Baranac-Stojanović, M., Tatar, J., Stojanović, M.,& Marković, R.. (2010). Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 66(34), 6873-6884.
https://doi.org/10.1016/j.tet.2010.06.057
Baranac-Stojanović M, Tatar J, Stojanović M, Marković R. Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles. in Tetrahedron. 2010;66(34):6873-6884.
doi:10.1016/j.tet.2010.06.057 .
Baranac-Stojanović, Marija, Tatar, Jovana, Stojanović, Milovan, Marković, Rade, "Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles" in Tetrahedron, 66, no. 34 (2010):6873-6884,
https://doi.org/10.1016/j.tet.2010.06.057 . .

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