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Molecular structures of syn- and anti-20-carboethoxyhydrazone isomers of 3Β, 21-diacetoxypregna-5,16-dien-20-one

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

Abstract

The validity of syn- and anti-isomer assignments in the case of 3Β,21-diacetoxypregna-5, 16-dien-20-one 20-carboethoxyhydrazones has been established by x-ray structural analysis; the isomer designations had been made previously based on chemical and spectral data. The isomers differ sharply in the conjugative relationship between the hydrazone group and the C16=C17 double bond in the steroid skeleton: the syn-isomer is trans-conjugated (the degree of twisting about the C17-C20 bond is characterized by a torsional angleψ=-161.0‡), while the anti-isomer is not conjugated (ϕ=− 75.3‡); this explains the electronic spectral features of these isomers.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organometallic Compounds, Academy of Sciences of the USSR, Moscow

    S. V. Lindeman, A. M. Turuta, Yu. T. Struchkov & A. V. Kamernitskii

Authors
  1. S. V. Lindeman
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  2. A. M. Turuta
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  3. Yu. T. Struchkov
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  4. A. V. Kamernitskii
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 610–615, March, 1991.

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Lindeman, S.V., Turuta, A.M., Struchkov, Y.T. et al. Molecular structures of syn- and anti-20-carboethoxyhydrazone isomers of 3Β, 21-diacetoxypregna-5,16-dien-20-one. Russ Chem Bull 40, 529–533 (1991). https://doi.org/10.1007/BF00957989

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  • DOI: https://doi.org/10.1007/BF00957989

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