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Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): IX. Noncatalytic Reactions with Alkylarenes

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Abstract

The reaction of 1,3-dehydroadamantane with alkylbenzenes was studied for the first time. It involved the C–H bond of the alkyl substituent in the α-position with respect to the aromatic ring. The proposed radical mechanism of the reaction was confirmed by the isolation of 1,1′-biadamantane and 1,2-diphenylethane derivatives. Difficultly accessible (adamantan-1-ylmethyl)arenes were synthesized in 53–78% yields.

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Authors and Affiliations

  1. Volzhsky Polytechnic Institute (Branch), Volgograd State Technical University, Volzhsky, 404121, Volgograd oblast, Russia

    G. M. Butov & E. A. Zubovich

  2. Volgograd State Technical University, 400131, Volgograd, Russia

    G. M. Butov & V. M. Mokhov

Authors
  1. G. M. Butov
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  2. V. M. Mokhov
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  3. E. A. Zubovich
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Correspondence to G. M. Butov.

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For communication VIII, see [1].

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Butov, G.M., Mokhov, V.M. & Zubovich, E.A. Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): IX. Noncatalytic Reactions with Alkylarenes. Russ J Org Chem 56, 1041–1045 (2020). https://doi.org/10.1134/S1070428020060123

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