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Issue 0, 1968
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Proton chemical shifts of some halogenated steroids and t-butylcyclohexanes


The chemical shifts of protons α, β, and γ to the halogen atoms in 9α-halogeno-11β-hydroxyprogesterone, 2β-halogeno-3α-hydroxy-5α-cholestane, and trans-2-halogeno-trans-5-t-butylcyclohexanols have been measured in dilute carbon tetrachloride solutions. The chemical shifts of the α- and β-protons can be correlated with electronegativity after allowing for a calculated ‘C–C bond shift’. The chemical shift of the C(10)-methyl group, which is γ to the halogen atom in 9α-halogeno-11β-hydroxyprogesterone, appears to be controlled by increasing size of the substituent, unlike the γ protons in the 1-halogenoadamantane series with fixed stereochemistry which follows the order expected for electronegativity. The possibility that trans-2-halogeno-trans-5-t-butychyclohexanol may not exist in the true chair conformation is also discussed.

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Article information

J. Chem. Soc. B, 1968, 721-725
Article type

Proton chemical shifts of some halogenated steroids and t-butylcyclohexanes

R. E. Lack and A. B. Ridley, J. Chem. Soc. B, 1968, 721
DOI: 10.1039/J29680000721

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