Issue 3, 1984

Rate constants for the formation of oxiranes by γ-scission in secondary β-t-butylperoxyalkyl radicals

Abstract

Rate constants for the title reactions have been determined from the ratios of oxirane to peroxide obtained in the reductions of β-bromoalkyl t-butyl peroxides with tributyltin hydride. At ca. 298 K the rate constants are 0.32, 1.12, 1.96, 2.0, and 6.2 × 106 s–1 for β-t-butylperoxy derivatives of trinorbornan-2-yl (exo) cyclohexyl, 1-methylpropyl, cyclopentyl, and 1-ethylbutyl, respectively. The results are discussed in terms of steric and electronic effects in the transition state leading to ring closure of the radicals.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1984, 523-527

Rate constants for the formation of oxiranes by γ-scission in secondary β-t-butylperoxyalkyl radicals

A. J. Bloodworth, J. L. Courtneidge and A. G. Davies, J. Chem. Soc., Perkin Trans. 2, 1984, 523 DOI: 10.1039/P29840000523

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