Stereochemical evidence suggests that acid-catalysed citran formation proceeds via electrocyclisation of a dienone; pyrolysis of ‘farnesylidenemalonic acid’ proceeds with retention of configuration at the newly formed 8-olefin bond, indicating the operation of a retro-Diels–Alder process.
L. Crombie, S. D. Redshaw and D. A. Whiting, J. Chem. Soc., Chem. Commun., 1979, 630 DOI: 10.1039/C39790000630
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