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.
TY - JOUR
AU - Baranac-Stojanović, Marija
AU - Tatar, Jovana
AU - Stojanović, Milovan
AU - Marković, Rade
PY - 2010
UR - http://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 - Pergamon-Elsevier Science Ltd, Oxford
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",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/700",
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 = "Pergamon-Elsevier Science Ltd, Oxford",
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.
Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 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. Tetrahedron. 2010;66(34):6873-6884
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" Tetrahedron, 66, no. 34 (2010):6873-6884,
https://doi.org/10.1016/j.tet.2010.06.057 .
