The reaction of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt) with 1,2:5,6-di-O-isopropylidene-a-D-glucose

Abstract

The treatment of 1,2:5,6-di-O-isopropylidene-α-D-glucose with N-dichloromethylene-N,N-dimethyl ammonium chloride (Viehe's salt) (2: 1 or 1 : 1) gives two iminium salts. These are readily hydrolysed to a carbonate and a carbamate. Treatment with sodium hydrogen sulfide gave some thiocarbonate and thiocarbamate. One of the iminium salts underwent a base-induced elimination to give 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-ribo-hex-3-enofuranose.