The reactions of nitrosyl chloride and dinitrogen tetroxide with acetylated glycals. Acetylated 2-deoxy-2-nitroso-α-D-hexopyranosyl chlorides and nitrates and acetylated 2-nitroglycals

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Abstract
Reaction of nitrosyl chloride with acetylated glycals affords, with a high degree of stereospecificity, dimeric acetylated 1,2-cis-2-deoxy-2-nitroso-α-D-aldopyranosyl chlorides. Reaction of acetylated glycals with dinitrogen tetroxide, depending on the reaction conditions, can give either acetylated 2-deoxy-2-nitroso-α-D-aldopyranosyl nitrates as dimers or acetylated 2-nitroglycals. The mechanisms of these reactions are discussed.