List references from the University of Geneva Physical Chemistry reference database

Rearrangement of cholesta-2,4,6-triene in the presence of p-toluenesulfonic acid in acetic acid at 70Â Â°C leads to 4-methyl-19-nor-cholesta-1,3,5(10)-triene and 1(10Â â†’Â 6)-abeo-14Î²-cholesta-5,7,9(10)-triene in less than 2Â h. Postulated mechanisms of formation of these products are supported by molecular mechanics calculations of the relative stabilities of reaction intermediates. The results suggest that Î”^5,7-sterols, the most common natural precursors of triunsaturated steroidal hydrocarbons in contemporary sediments, constitute another major source for monoaromatic A and B steroids in addition to Î”⁵-sterols.

Acid catalysed backbone rearrangement of cholesta-2,4,6-triene: On the origin of ring A and ring B aromatic steroids in recent sediments P. Schüpfer, Y. Finck, F. Houot and F.O. Gülaçar Organic Geochemistry, 38 (4) (2007), p671-681 DOI:10.1016/j.orggeochem.2006.11.004 \| unige:3587 \| Abstract \| Article HTML \| Article PDF
Rearrangement of cholesta-2,4,6-triene in the presence of p-toluenesulfonic acid in acetic acid at 70Â Â°C leads to 4-methyl-19-nor-cholesta-1,3,5(10)-triene and 1(10Â â†’Â 6)-abeo-14Î²-cholesta-5,7,9(10)-triene in less than 2Â h. Postulated mechanisms of formation of these products are supported by molecular mechanics calculations of the relative stabilities of reaction intermediates. The results suggest that Î”^5,7-sterols, the most common natural precursors of triunsaturated steroidal hydrocarbons in contemporary sediments, constitute another major source for monoaromatic A and B steroids in addition to Î”⁵-sterols.

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