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

✍ Scribed by Jean M. J. Tronchet; Faranak Rachidzadeh; Jeannine Tronchet

Publisher
John Wiley and Sons
Year
1974
Tongue
German
Weight
220 KB
Volume
57
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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