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Study of the rotational isomerism about the C-O bond in six-membered secondary-tertiary diols

  • Physical Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

We have determined the spectroscopic characteristics, the dipole moments, and the Kerr constants of the stereoisomers of the secondary-tertiary diols of the cyclohexane and bicyclo [4.1.0]pentane series: 3Β,4α-dihydroxy-3-carane (I), 3Β,4α-dihydroxy-3-methylnorcarane (II), 3α,4Β-dihydroxy-3-methylnorcarane (III), 4α, 5Β-dihydroxy-3-methylcyclohexene (IV), 3Β,4α-dihydroxy-3-carane (V), 3Β,4Β-dihydroxy-3-methylnorcarane (VI), 3α, 4α-dihydroxy-3-carane (VII), and 3α,4α-dihydroxy-4-methyl-3-carane (VIII). It was found that the cis diols are more polar than their trans isomers. It was shown by electrical and electrooptical methods that rotamers with a gauche orientation with respect to the tertiary C-O are stable relative to those containing the diol at the ordinary C-C bond of the ring.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, USSR Academy of Sciences, USSR

    É. Kh. Kazakova, S. V. Andreeva, G. I. Kovylyaeva, G. A. Bakaleinik & A. N. Vereshchagin

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  1. É. Kh. Kazakova
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  2. S. V. Andreeva
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  3. G. I. Kovylyaeva
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  4. G. A. Bakaleinik
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  5. A. N. Vereshchagin
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Deceased.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 619–625, March, 1991.

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Kazakova, É.K., Andreeva, S.V., Kovylyaeva, G.I. et al. Study of the rotational isomerism about the C-O bond in six-membered secondary-tertiary diols. Russ Chem Bull 40, 538–543 (1991). https://doi.org/10.1007/BF00957991

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  • DOI: https://doi.org/10.1007/BF00957991

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