Journal of the Chemical Society. Perkin transactions II p. 1371 - 1376 (1988)
Update date:2022-08-16
Topics:
Walton, John C.
Free radicals abstract hydrogen from both the bridge and bridgehead sites in bicyclo<2.2.0>hexane (4).The bicyclo<2.2.0>hexan-1-yl radical was observed by e.p.r. spectroscopy.The bicyclo<2.2.0>hexan-2-yl radical rearranges by stereoelectronically forbidden β-scission to give cyclohex-3-enyl radicals.Unlike other cyclobutanes, compound (4) undergoes an SH2 reaction with bromine atoms.Free radicals abstract hydrogen only from the methylene groups of the C5 ring in bicyclo<3.2.0>heptane (15a).The bicyclo<3.2.0>heptan-2-yl radicals were observed by e.p.r. spectroscopy, as was their rearrangement, by stereoelectronically allowed β-scission, to 2-(cyclopent-2-enyl)ethyl radicals.Bromine atoms abstract hydrogen from (15a) and no SH2 reaction was detected.The radicals and their rearrangements were studied by semi-empirical MINDO/3 and MNDO methods.
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