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Synthesis and Transformations of Aryl-Substituted Alkenes of the Adamantane Series

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Abstract

Aryl-substituted alkenes of the adamantane series, 1-[(Z,E)-3-phenylprop-2-en-1-yl]adamantane and 1-[(Z)-3-phenylprop-1-en-1-yl]adamantane, have been synthesized by the Wittig reaction. Their allylic bromination involves two concurrent reactions, radical substitution and raical addition. The different chemical behaviors of the aryl-substituted alkenes have been demonstrated in the Ritter reaction. Depending on the alkene structure and acid catalyst nature, the products are secondary amides, sulfonic acid derivatives, and homoadamantane γ-sultone.

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Authors and Affiliations

  1. Samara State Technical University, ul. Molodogvardeiskaya 244, Samara, 443100, Russia

    S. A. Savel’eva, M. V. Leonova, M. R. Baimuratov & Yu. N. Klimochkin

Authors
  1. S. A. Savel’eva
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  2. M. V. Leonova
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  3. M. R. Baimuratov
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  4. Yu. N. Klimochkin
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Correspondence to S. A. Savel’eva.

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Original Russian Text © S.A. Savel’eva, M.V. Leonova, M.R. Baimuratov, Yu.N. Klimochkin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 7, pp. 994–1000.

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Savel’eva, S.A., Leonova, M.V., Baimuratov, M.R. et al. Synthesis and Transformations of Aryl-Substituted Alkenes of the Adamantane Series. Russ J Org Chem 54, 996–1002 (2018). https://doi.org/10.1134/S1070428018070047

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  • DOI: https://doi.org/10.1134/S1070428018070047

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