Abstract
Reactions of C5–C12 cycloalkyl radicals and carbenes produced during radiolysis, vacuum-u.v. photolysis, and decomposition of cycloalkanone p-tosylhydrazones were investigated. The disproportionation to combination ratios of radicals are ca. 1 and agree with the ratios of linear secondary radicals. The disproportionation of smaller cycloalkyl radicals yields cis-cycloalkenes and cycloalkanes; from C9 and C10cis- and trans-cycloalkenes and cycloalkanes and from C11 and C12trans-cycloalkenes and cycloalkanes are produced. Both atoms of H2 given off in the elimination reaction from excited cycloalkane molecules originate from the same carbon atom and in this process carbenes are formed. Rearrangement of small (C5, C6) and large (C11, C12) cycloalkylcarbenes in the solvent of the given cycloalkane occurs by 1,2-hydrogen migration. C7–C10 carbenes rearrange both by hydrogen atom migration and transannular insertion.
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