Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles
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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
- Pergamon-Elsevier Science Ltd, Oxford