Journal of the Chemical Society. Perkin transactions II p. 661 - 668 (1983)
Update date:2022-09-26
Topics:
Beckwith, Athelstan L. J.
Easton, Christopher J.
Thermolysis of the peroxyoxalates (1)-(7) and the diacyl peroxides (8)-(11) in cyclohexane at 100 deg C gives cycloalkenes and cycloalkanes by hydrogen-atom transfer reactions of the initially formed conformationally biased 4-t-butyl-, 4-t-butyl-cis,cis-2,6-dimethyl-, 4-t-butyl-cis,trans-2,6-dimethyl-, 4-t-butyl-cis-2-methyl-, 4-t-butyl-trans-2-methyl-, and 5-t-butyl-cis-2-methylcyclohexyl radicals (12)-(17).The composition of the product mixtures indicates that transfer of axial β-hydrogen atoms occurs more rapidly than does transfer of equatorial β-hydrogen atoms.These results support the hypothesis that homolytic fission of a C-H bond is favoured when it lies chlose to the plane of an adjacent semi-occupied orbital.
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