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Heteryladamantanes. Communication 3. Synthesis of 3-(1-adamantyl)-2-methyl-3-chloropropenal and related o-methyl-substituted heteryladamantanes

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

Conclusions

  1. 1.

    3-(1-Adamantyl)-2-methyl-3-chloropropenal has been synthesized for the first time by chloroformylation of 1-adamantyl ethyl ketone. It is a convenient synthon for obtaining o-methyl-substituted heteryladamantanes.

  2. 2.

    3-(1-Adamantyl)-2-methyl-3-chloropropenal is formed as a mixture of Z and E isomers with the latter predominating [in contrast to the Z form of 3-(1-adamantyl)-3-chloropropenal].

  3. 3.

    Similarities and differences in the characteristics of 3-(1-adamantyl)-2-methyl-3-chloropropenal and 3-(1-adamantyl)-3-chloropropenal are discussed.

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Literature cited

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Authors and Affiliations

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

    V. S. Dermugin, V. I. Shvedov & V. P. Litvinov

Authors
  1. V. S. Dermugin
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  2. V. I. Shvedov
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  3. V. P. Litvinov
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Additional information

For Communication 2 see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2549–2554, November, 1985.

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Dermugin, V.S., Shvedov, V.I. & Litvinov, V.P. Heteryladamantanes. Communication 3. Synthesis of 3-(1-adamantyl)-2-methyl-3-chloropropenal and related o-methyl-substituted heteryladamantanes. Russ Chem Bull 34, 2362–2366 (1985). https://doi.org/10.1007/BF00956801

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  • DOI: https://doi.org/10.1007/BF00956801

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