Un nouveau type de sucres azotés,les gem-azo-alcools. Communication préliminaire

Treatment of keto-sugar p-nitrophenylhydrazones with lead tetraacetate led to the corresponding gem-azo-acetates. The reaction is highly stereoselective, only one of the two possible epimers at the new asymmetric carbon being formed in measurable quantity. Catalytic de-acylation of these gem-azo-acetates yielded, quantitatively, representatives of a new class of nitrogen-containing sugars: the gem-azo-alcohols. When treated with potassium t-butylate, the gem-azoacetates underwent a rearrangement with ring expansion leading to N-aminolactams.