Some anomalous products from the attempted halogenation of unsaturated alcohols by the complex from dimethyl sulphide and N-halogenosuccinimide

Abstract

Intramolecular participation of carbon–carbon double bonds and hydroxy-groups can occur when alcohols are treated with complexes derived from dimethyl sulphide and N-halogenosuccinimides. 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.