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Mass spectrometry of steroid systems

Communication 18. Cis-transisomerism of model carbo- and heterocyclic compounds

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

Conclusions

  1. 1.

    The mass spectra of four cis-trans-isomers of the sclaerol oxide series (I)–(IV), ambreinolide and its cis-A/B-isomer, as well as their bicyclic analogs: cis- and trans-2,5, 5, 1a-hexamethyl-1a, 4a, 5, 6, 7, 8-hexahydro-γ chromene, cis- and trans- Δ8-4, 4, 8, 10-tetramethyl-9-(β-carboxyethyl)octaline, and cis- and trans-Δ8-4, 4, 8, 10-tetramethyl-9-(3'-ketobutyl-1')octaline were studied.

  2. 2.

    In the case of cis- and trans-isomers differing in the type of joining of the carbocyclic rings, the intensity of the peaks due to elimination of a CH3 from the molecular ion or bicyclic fragment containing the A and B rings is greater in the case of cis-compounds.

  3. 3.

    The mass spectra of cis- and trans-joined compounds, one of the rings of which contained a heteroatom (III) and (IV), (VII)–(X), in contrast to their carbocyclic analogs, differ substantially from one another also in the intensity of the peaks of the ions due to cleavage of the bond at the site of joining of the rings.

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Literature cited

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Authors and Affiliations

  1. Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR, USSR

    N. S. Vul'fson, V. I. Zaretskii, V. L. Sadovskaya & G. E. Muntyan

Authors
  1. N. S. Vul'fson
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  2. V. I. Zaretskii
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  3. V. L. Sadovskaya
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  4. G. E. Muntyan
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Additional information

For communication 17, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1521–1526, July, 1968.

The authors would like to express their deep gratitude to A. N. Semenovskii and V. A. Smit for providing the compounds and for their participation in the discussion of the results.

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Vul'fson, N.S., Zaretskii, V.I., Sadovskaya, V.L. et al. Mass spectrometry of steroid systems. Russ Chem Bull 17, 1431–1436 (1968). https://doi.org/10.1007/BF00907839

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  • DOI: https://doi.org/10.1007/BF00907839

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