Abstract
IN a recent paper1, it was reported that the cis-chloride is formed in preference to the trans-chloride when 4-tert-butylcyclohexyl radicals react with the corresponding carbinyl hypochlorite. This specificity was interpreted in terms of a preferred pyramidal arrangement of groups about the free-radical carbon such that the unpaired electron occupies an orbital having considerable carbon 2s-character. No reason was given, however, for the preference of one of these pyramidal arrangements over the other1.
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References
Greene, F. D., Chu, C.-C., and Walia, J., J. Amer. Chem. Soc., 84, 2463 (1962).
McConnell, H. M., and Fessenden, R. W., J. Chem. Phys., 31, 1688 (1959).
See, for example, Symons, M. C. R., Adv. Phys. Org. Chem., edit. by Gold, V., 1, 284 (1963).
Atkins, P. W., Keen, N., and Symons, M. C. R., J. Chem. Soc., 250 (1963).
Fessenden, R. W., Quart. Rep. Mellon Inst., April-June (1961).
Symons, M. C. R., Tetrahedron, 18, 333 (1962).
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SYMONS, M. Relation between Stereochemistry and Reactivity of Organic Free-radicals. Nature 198, 1196–1197 (1963). https://doi.org/10.1038/1981196a0
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DOI: https://doi.org/10.1038/1981196a0
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