List references from the University of Geneva Physical Chemistry reference database

Rearrangement of 5Î±- and 5Î²-cholesta-6,8(14)-dienes (13aÂ andÂ 13b, resp.) in the presence of anhydrous toluene-4-sulfonic acid in acetic acid leads to 5Î±- and 5Î²-12(13Â â†’Â 14)-abeo-cholesta-8,13(17)-dienes (15aÂ andÂ 15b, resp.)Â viaÂ 5Î±- and 5Î²-cholesta-8,14-dienes (14aÂ andÂ 14b, resp.), respectively. Epimerization at C(20) of the spirosteradienesÂ 15aÂ andÂ 15bÂ 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.

Acid-catalysed backbone rearrangement of cholesta-6,8(14)-diene L. Rong-Ming, X.F.D. Chillier, P. Kamalaprija, U. Burger and F.O. Gülaçar Helvetica Chimica Acta, 79 (4) (1996), p989-998 DOI:10.1002/hlca.19960790407 \| unige:2833 \| Abstract \| Article PDF
Rearrangement of 5Î±- and 5Î²-cholesta-6,8(14)-dienes (13aÂ andÂ 13b, resp.) in the presence of anhydrous toluene-4-sulfonic acid in acetic acid leads to 5Î±- and 5Î²-12(13Â â†’Â 14)-abeo-cholesta-8,13(17)-dienes (15aÂ andÂ 15b, resp.)Â viaÂ 5Î±- and 5Î²-cholesta-8,14-dienes (14aÂ andÂ 14b, resp.), respectively. Epimerization at C(20) of the spirosteradienesÂ 15aÂ andÂ 15bÂ 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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