Issue 15, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Stereoselectivity, regioselectivity and mechanism in the intramolecular ‘citran’ bicyclisation of chromenes †

Cesar Calderon-Higginson,a   Leslie Crombie,a   Sally D. Redshawa  and  Donald A. Whiting*a  

* Corresponding authors

a Department of Chemistry, The University of Nottingham, Nottingham, UK

Abstract

Stereochemical evidence suggests that acid catalysed citran formation proceeds via electrocyclisation of a dienone, and that pyrolysis of ‘farnesylidenemalonic acid’ proceeds with retention of configuration at the newly formed 8-olefin bond, indicating the operation of forward and reverse Diels–Alder processes respectively; 1,3-dihydroxynaphthalene reacts with citral in pyridine to yield chromene and citran products in a regioselective fashion.

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Article information

DOI
https://doi.org/10.1039/B001310M
Article type
Paper
Submitted
17 Feb 2000
Accepted
17 May 2000
First published
14 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2491-2494

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Stereoselectivity, regioselectivity and mechanism in the intramolecular ‘citran’ bicyclisation of chromenes

C. Calderon-Higginson, L. Crombie, S. D. Redshaw and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 2000, 2491 DOI: 10.1039/B001310M

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