Title of article :
Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles
Author/Authors :
Marija Baranac-Stojanovi?، نويسنده , , Jovana Tatar، نويسنده , , Milovan Stojanovi?، نويسنده , , Rade Markovi?، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 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 Ph3P, AcS−, CN−, I−, F−, Ac2CH− and N3− the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et3N 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 :
Bromophilic reaction , rearrangement , Carbanion , 4-Oxothiazolidine , vinyl bromide
Journal title :
Tetrahedron
Journal title :
Tetrahedron