Jump to main content
Jump to site search

Issue 20, 2003
Previous Article Next Article

A tricycloheptane product in cationic rearrangements

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 05 Aug 2003, accepted on 02 Sep 2003 and first published on 19 Sep 2003


Article type: Paper
DOI: 10.1039/B309329H
Citation: Org. Biomol. Chem., 2003,1, 3570-3571
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements