Radical reactions of bicyclo[2.1.0]pentane

  1. Get@NRC: Radical reactions of bicyclo[2.1.0]pentane (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1039/P29800001366
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Journal titleJournal of the Chemical Society, Perkin Transactions 2
Pages13661371; # of pages: 6
AbstractThe 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.
Publication date
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276685
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Record identifiere70e17ef-1126-49c5-bf9b-95d855e3659d
Record created2015-10-13
Record modified2016-05-09
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