Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles
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. (C) 2010 Elsevier Ltd. All rights reserved.
Keywords:
4-Oxothiazolidine / Vinyl bromide / Bromophilic reaction / Carbanion / RearrangementSource:
Tetrahedron, 2010, 66, 34, 6873-6884Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-MESTD-MPN2006-2010-142007)
DOI: 10.1016/j.tet.2010.06.057
ISSN: 0040-4020
WoS: 000280953500026
Scopus: 2-s2.0-77955469036
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Baranac-Stojanović, Marija AU - Tatar, Jovana AU - Stojanović, Milovan AU - Marković, Rade PY - 2010 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1102 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. (C) 2010 Elsevier Ltd. All rights reserved. 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", 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. (C) 2010 Elsevier Ltd. All rights reserved.", 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. in 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. 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 . .