Preparation of acetylated 2,6-anhydrohept(hex)-2-enononitriles (1-cyano-2-hydroxyglycals)

Article abstract of DOI:10.1016/0008-6215(91)84157-A

The reactions of acetylated 1-bromo-D-glycosyl cyanides with acetate³ and thiolates have been described, and reactions with cyanides are now reported. The mechanism of the formation of the lactones is unclear. Oxidative decyanation of nitriles to give ketones and other carbonyl compounds in the presence of a strong base is well documented. Compounds of the type ArRC(I)CN were converted into ArRC = O with silver oxide in tetrahydrofuran, whereas the corresponding bromides were inert. In these reactions, air is the source of the oxygen. Since the transformations reported here give the lactones in an atmosphere of nitrogen, methyl sulfoxide may be the oxidising agent.