The Transformations of Dimeric Tri-O-acetyl-2-deoxy-2-nitroso-α-D-hexopyranosyl Chlorides in Dimethylformamide

Abstract

The dimeric nitrosyl chloride adducts of tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1- and D-lyxo-hex-1- enitols (glycals) dissociate in dimethylformamide to the monomeric forms which rapidly isomerize to the corresponding tri-O-acetyl-2-oximino-α-D-hexopyranosyl chlorides. Evidence is provided for the dehydrochlorination of these latter compounds to highly reactive tri-O-acetyl-1,5-anhydro-2-deoxy-2-nitroso-D-hex-1-enitols.