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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

C Copeland and RV Stick

Australian Journal of Chemistry 35(11) 2269 - 2275
Published: 1982

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.

https://doi.org/10.1071/CH9822269

© CSIRO 1982

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