The Deamination of the 3α- and 3β-Aminocholestanes and their Amide Derivatives

The nitroso acetamides, naphthamides, and benzylcarbamates of 3α- and 3β-aminocholestanes were decomposed in various solvents and the nitrous acid deaminations of the free amines in acetic acid and aqueous acetic acid mixtures were studied. In these reactions the intramolecular process leads to prod...

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Bibliographic Details
Published in:Canadian journal of chemistry 1972-02, Vol.50 (3), p.364-370
Main Authors: Bachelor, F. W, White, E. H
Format: Article
Language:English
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Summary:The nitroso acetamides, naphthamides, and benzylcarbamates of 3α- and 3β-aminocholestanes were decomposed in various solvents and the nitrous acid deaminations of the free amines in acetic acid and aqueous acetic acid mixtures were studied. In these reactions the intramolecular process leads to products with high degrees of retention of configuration, whereas the intermolecular process leads to products which are predominantly equatorial. Diazoalkanes were shown not to be intermediates in these deaminations.
ISSN:0008-4042
1480-3291
DOI:10.1139/v72-054