Rearrangement in the solvolysis of some carbohydrate nitrobenzene-p-sulphonates

Abstract

Hydrolysis of methyl 3-O-nitrobenzene-p-sulphonyl-α-D-mannopyranoside and -glucopyranoside yields methyl 3-deoxy-3-formyl-α-D-lyxofuranoside and -xylofuranoside, respectively. These are also produced by deamination of the corresponding 3-amino-3-deoxy-compounds with nitrous acid. 2,5-Anhydro-D-mannose results from hydrolysis of methyl 2-O-nitrobenzene-p-sulphonyl-α-D-glucoside.