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Acid-catalysed backbone rearrangement of cholesta-6,8(14)-diene

Rong-Ming, Liu
Published in Helvetica Chimica Acta. 1996, vol. 79, no. 4, p. 989-998
Abstract Rearrangement of 5- and 5-cholesta-6,8(14)-dienes (13a and 13b, resp.) in the presence of anhydrous toluene-4-sulfonic acid in acetic acid leads to 5- and 5-12(13 14)-abeo-cholesta-8,13(17)-dienes (15a and 15b, resp.) via 5- and 5-cholesta-8,14-dienes (14a and 14b, resp.), respectively. Epimerization at C(20) of the spirosteradienes 15a and 15b occurs with increasing reaction time. Molecular-mechanics calculation of the relative stabilities of these compounds and of congeners thereof is in agreement with the observed reaction pathway.
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Research group Groupe Gülaçar
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RONG-MING, Liu et al. Acid-catalysed backbone rearrangement of cholesta-6,8(14)-diene. In: Helvetica Chimica Acta, 1996, vol. 79, n° 4, p. 989-998. https://archive-ouverte.unige.ch/unige:2833

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Deposited on : 2009-09-21

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