Carbon-bromine cleavage by dimethyl sulfoxide: the key step of C(5) functionalization of push-pull 2-alkylidene-4-oxothiazolidine vinyl bromides

Push-pull 2-alkylidene-4-oxothiazolidine vinyl bromides undergo efficient C(5) functionalization through DMSO-assisted carbon-bromine cleavage, followed by a bromine transfer-substitution (or elimination) sequence. A mechanism for this novel transformation is proposed.