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Chemical Transformations of Tetracyclo[3.3.1.1.3,7.0.1,3]decane (1,3-Dehydroadamantane): VIII. Reaction of 1,3-Dehydroadamantane with Aliphatic Aldehydes

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Abstract

The reaction of 1,3-dehydroadamantane with aliphatic aldehydes involves the Ca-H bond and forms hardly accessible branched 2-(1-adamantyl)alkylaldehydes in one stage in a yield of 60-78%. It is found that 2-(1-adamantyl)alkylaldehydes are prone to oligomerization. The reaction of 2-(1-adamantyl)-alkylaldehydes with 2,4-dinitrophenylhydrazine gave the corresponding hydrazones in a yield of 84-98%.

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Authors and Affiliations

  1. Volgograd State Technical University, pr. Lenina 28b, Volgograd, 400131, Russia

    V. M. Mokhov, G. Yu. Parshin & G. M. Butov

  2. Volzhsky Polytechnic Institute (Branch), Volgograd State Technical University, ul. Engelsa 42, Volzhskii, Volgograd obl., 404121, Russia

    K. R. Saad & G. M. Butov

Authors
  1. V. M. Mokhov
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  2. K. R. Saad
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  3. G. Yu. Parshin
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  4. G. M. Butov
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Corresponding authors

Correspondence to V. M. Mokhov or G. M. Butov.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 737–742.

For communication VII, see [1].

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Mokhov, V.M., Saad, K.R., Parshin, G.Y. et al. Chemical Transformations of Tetracyclo[3.3.1.1.3,7.0.1,3]decane (1,3-Dehydroadamantane): VIII. Reaction of 1,3-Dehydroadamantane with Aliphatic Aldehydes. Russ J Org Chem 55, 640–645 (2019). https://doi.org/10.1134/S1070428019050099

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  • DOI: https://doi.org/10.1134/S1070428019050099

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