113555-33-2Relevant articles and documents
Homolytic Rearrangements of Bicyclohexane and Bicycloheptane
Walton, John C.
, p. 1371 - 1376 (2007/10/02)
Free radicals abstract hydrogen from both the bridge and bridgehead sites in bicyclohexane (4).The bicyclohexan-1-yl radical was observed by e.p.r. spectroscopy.The bicyclohexan-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 bicycloheptane (15a).The bicycloheptan-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.
Radical Rearrangements of Bicyclohexane: Homolytic Substitution of a Cyclobutane Ring
Walton, John C.
, p. 1252 - 1254 (2007/10/02)
Bromine atoms react with bicyclohexane in an SH2 reaction at the bridgehead carbon atoms; the bicyclohex-2-yl radical rearranges by β-scission of the inter-ring bond.