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Issue 20, 2003
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A tricycloheptane product in cationic rearrangements

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The bicycloheptene 6 rearranged in acid to give the tricycloheptane 9, as shown by an X-ray crystal structure determination of the p-nitrobenzoate 10 derived from it. Earlier results in the literature had already indicated that this isomer was the thermodynamic sink. This apparently crowded structure, with its three contiguous quaternary centres, is, nevertheless, lower in energy than other accessible but less crowded structures, because of electronic stabilisation of the more substituted cyclopropane ring conjugated to the ester group.

Graphical abstract: A tricycloheptane product in cationic rearrangements

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Article information

05 Aug 2003
02 Sep 2003
First published
19 Sep 2003

Org. Biomol. Chem., 2003,1, 3570-3571
Article type

A tricycloheptane product in cationic rearrangements

J. E. Davies, I. Fleming and J. M. Goodman, Org. Biomol. Chem., 2003, 1, 3570
DOI: 10.1039/B309329H

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