Rearrangement of radicals derived from bicyclo[5.1.0]octa-2,4-diene, tricyclo[6.1.0.02,4]nona-6-ene and tetracyclo[7.1.0.02,4.05,7]decane

Peter N. Culshaw, Michael Dalton, Finlay MacCorquodale, John C. Walton*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

ESR spectra from bicyclo[5.1.0]octadienyl and tricyclo[6.1.0.02,4]nona-6-enyl radicals, and from the rearrangement of tetracyclo[7.1.0.02,4.05,7]decanyl radicals have been observed. The rate of ring opening increases in the stated order. The ESR parameters and semiempirical calculations suggest that electron delocalisation into the three-membered rings is insignificant. At temperatures above ambient the bicyclo[5.1.0]octadienyl radical rearranges to the cycloheptatrienylmethyl radical, which in turn rearranges to the norcaradienylmethyl radical and hence to the vinylcyclohexadienyl radical, which gives styrene and products derived therefrom. 1,3- Bromination via the SH2 reaction at the three-membered ring is also an important process for bicyclo[5.1.0]octa-2,4-diene.

Original languageEnglish
Pages (from-to)531-536
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number4
DOIs
Publication statusPublished - 1 Jan 1990

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