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Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): VI. Reactions of 1,3-Dehydroadamantane with Carboxylic Acid Chlorides

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Abstract

1,3-Dehydroadamantane reacted with saturated carboxylic acid chlorides to give the corresponding 1-acyl-3-chloroadmantanes as the major products. In some cases, minor products of insertion into the Cα–H bond of acyl chloride were formed. The reactions of 1,3-dehydroadamantane with aromatic (heteroaromatic) carboxylic acid chlorides selectively afforded aryl (hetaryl) 3-chloroadamantan-1-yl ketones. The described reactions provide a synthetic route to difficultly accessible alkyl (aryl) ketones containing a 3-chloroadamantan- 1-yl group in one step under mild conditions with high yields.

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Authors and Affiliations

  1. Volgograd State Technical University, pr. imeni Lenina 28, Volgograd, 400005, Russia

    V. M. Mokhov

  2. Volzhsky Polytechnic Institute (Branch), Volgograd State Technical University, ul. Engel’sa 42a, Volzhsky, Volgograd oblast, 404121, Russia

    G. M. Butov & K. R. Saad

Authors
  1. V. M. Mokhov
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  2. G. M. Butov
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  3. K. R. Saad
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Correspondence to G. M. Butov.

Additional information

Original Russian Text © V.M. Mokhov, G.M. Butov, K.R. Saad, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 6, pp. 840–843.

For communication V, see [1].

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Mokhov, V.M., Butov, G.M. & Saad, K.R. Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): VI. Reactions of 1,3-Dehydroadamantane with Carboxylic Acid Chlorides. Russ J Org Chem 54, 840–843 (2018). https://doi.org/10.1134/S1070428018060039

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  • DOI: https://doi.org/10.1134/S1070428018060039

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