Radical reactions of bicyclo[2.1.0]pentane

Campbell Jamieson, John C. Walton*, Keith U. Ingold

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

The photochemical reactions of bicyclo[2.1.0]pentane with bromine, bromotrichloromethane, t-butyl hypochlorite, di-t-butyl peroxide, and N-bromosuccinimide have been investigated. Trichloromethyl, t-butoxyl, and succinimidyl radicals abstract hydrogen from the C4 ring. The expected bicyclopentyl radicals were not detected and if they are discrete intermediates they must rearrange by fission of the C(1)-C(4) bond common to the two rings to form cyclopent-3-enyl radicals. The e.s.r. spectrum of the latter radicals was obtained. Bromine (and chlorine) atoms may abstract hydrogen, but their major pathway involves attack at the bridgehead carbon atoms in an S H2 reaction with fission of the C(1)-C(4) bond to give 3-halogenocyclopentyl radicals.

Original languageEnglish
Pages (from-to)1366-1371
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number9
Publication statusPublished - 1 Dec 1980

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