Unusual behaviour of some γ- and δ-lactones towards dichloromethylenation using tris(dimethylamino)phosphine–tetrachloromethane
Abstract
Lactones derived from D-glucose, D-mannose and L-ascorbic acid reacted unexpectedly with tris(dimethylamino)phosphine–tetrachloromethane to give, respectively, dichloroalkene, anomeric vinyl chloride or acyl chloride; this behaviour supports an ionic mechanism for the alkenation.