Telomers (n=3) of Vinylene Carbonate with Tetrachloromethane as Novel Synthetic Intermediates for Aldo-heptoses and -octoses

Abstract

Stereochemistry of four isomeric telomers (n=3) (3), arising from the free-radical telomerization of vinylene carbonate with carbon tetrachloride, was unequivocally established as all trans addition forms (3a, b, c and d), based on their conversions to the enolphosphates (4) and the heptitols (8). Synthetic potential of the telomers (3) for aldoheptoses and -octoses has been shown by transforming for example the isomer b into"racemic"D-glycero-L-gulo-and D-glycero-D-ido-heptoses and D-threo-D-ido-octose in reasonable yields.