Abstract
THE comparatively greater stability of cyclohexane over its immediately lower ring homologue with reference to strain has not been explained satisfactorily. Experiments now afford evidence in support of the multiplanar and consequently strain-free, stable character of the substituted cyclo-hexane ring1. So far, only one form of 1:1-dimethyl-cyclohexanone-3, was known2. Now it is found that by direct reduction of dimethyldihydroresorcinol by Clemmensen's method a ketone is obtained, which is different from the ketone described previously. 1: l-Dimethylcyclohexanone-3 obtained by Crossley and others gave a semicarbazone melting at 195°–203°, whereas the ketone now obtained gives a semicarbazone melting at 162° C. The existence of the ketone in two isomeric forms is in accordance with the expectation of a strain-free configuration of the substituted cyclohexane ring.
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References
J. Ind. Chem. Soc., 7, 277; 1931.
Léser, Bull. Soc. Chim., (3), 21, 547; 1899. Blanc, C. R., 144, 143, 1357; 1907. Crossley and Renouf, J. Chem. Soc., 91, 81; 1907.
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QUDRAT-I-KHUDA, M. Strainless Monocyclic Rings. Nature 132, 210 (1933). https://doi.org/10.1038/132210a0
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DOI: https://doi.org/10.1038/132210a0
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