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

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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:
  • Pergamon-Elsevier Science Ltd, Oxford
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
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/700
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