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 3P, AcS −, CN −, I −, F −, Ac 2CH − 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 3N 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.
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