Some Anomalous Products from the Attempted Halogenation of Unsaturated Alcohols by the Complex from Dimethyl Sulphide and N-Halogenosuccinimide

Intramolecular participation of carbon-carbon double bonds and hydroxy-groups can occur when alcohols are treted with complexes derived from dimethyl sulphide and N-halogenosuccinimide. Neighbouring group participation is more common in the reactions in which N-bromosuccinimide rather than N-chlorosuccinimide is employed, the results suggest caution when the alcohol to halide conversion is attempted in certain polyfunctional molecules.