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The photochemistry of acetylene compounds. 14. Two types of acetylene addition to steroid 4-en-3-ones

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

Conclusions

  1. 1.

    The photochemical [2+2]-cycloaddition of 4-cholesten-3-one and testosterone to acetylene yields a mixture of 4β,5β-cycloadducts and 4α,5α-cycloadducts in ∼1∶5 ratio. The efficiency and sterospecificity of the cycloaddition are lower than found for the analogous reaction of steroid 4-en-3-ones with ethylene.

  2. 2.

    In addition to the cycloaddition, formation of “acyclic” 1∶1 adducts (steroid 4-ethylidene-5-en-3-ones) occurs.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    É. P. Serebryakov

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  1. É. P. Serebryakov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2313–2317, October, 1979.

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Serebryakov, É.P. The photochemistry of acetylene compounds. 14. Two types of acetylene addition to steroid 4-en-3-ones. Russ Chem Bull 28, 2134–2138 (1979). https://doi.org/10.1007/BF00947567

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  • DOI: https://doi.org/10.1007/BF00947567

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