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Heteroaryladamantanes. Communication 2. Structure of 3-(1-adamantyl)-3-chloropropenal and the synthesis of related adamantyl-substituted nitrogen heterocycles

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

Conclusions

  1. 1.

    3-(1-Adamantyl)-3-chloropropenal is a useful synthon for obtaining adamantyl-substituted nitrogen heterocycles: 2-(1-adamantyl)quinoline, 2-(1-adamantyl)-6-bromoquinoline, 6-(1-adamantyl)pyrimidine, 1-phenyl-5-(1-adamantyl)pyrazole, and 6-(1-adamantyl)thieno[2,3-e]pyrimidin-4-one.

  2. 2.

    X-ray crystallographic analysis points to the trans configuration of the aldehydic and adamantyl substituents on the C=C double bond in the molecule of 3-(1-adamantyl)-3-chloropropenal which is characterized by near Cs symmetry. A small increase in the C-Cl bond length in this molecule is probably due to a weak intermolecular attractive interaction at a distance of 3.447(2) Å.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, USSR

    V. P. Litvinov, V. S. Dermugin, V. I. Shvedov, V. E. Shklover & Yu. T. Struchkov

  2. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    V. P. Litvinov, V. S. Dermugin, V. I. Shvedov, V. E. Shklover & Yu. T. Struchkov

Authors
  1. V. P. Litvinov
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  2. V. S. Dermugin
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  3. V. I. Shvedov
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  4. V. E. Shklover
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  5. Yu. T. Struchkov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1858–1863, August, 1985.

For Communication 1, see [1].

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Litvinov, V.P., Dermugin, V.S., Shvedov, V.I. et al. Heteroaryladamantanes. Communication 2. Structure of 3-(1-adamantyl)-3-chloropropenal and the synthesis of related adamantyl-substituted nitrogen heterocycles. Russ Chem Bull 34, 1708–1713 (1985). https://doi.org/10.1007/BF00948522

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  • DOI: https://doi.org/10.1007/BF00948522

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