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Selective reductive dimerization of homocubane series oximes

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Abstract

The mixture of di- and monoethylene ketals obtained by the reaction of 1,9-dibromopentacyc lo[5.4.0.02,6.03,10.05,9]-undeca-8,11-dione followed by hydrolysis and ring contraction by Faworsky method was converted into a mixture of ethylene ketals of 7-bromopentacyclo[5.3.0.02,5.03,9.04,8]decan-6-one-4- and 5-bromopentacyclo[5.3.0.02,5.03,9.04,8]decan-6-one-8-carboxylic acid where the carboxy group was replaced by bromine along the procedure of Hunsdiecker-Borodine-Cristol. 6-Ethylene ketal of the pentacyclo[5.3.0.02,5.03,9.04,8] decan-6-one obtained by the debromination of ethylene ketals of 4,7- and 5,8-dibromopentacyclo[5.3.0.02,5.03,9.04,8] decan-6-one was hydrolyzed to ketone whose oxime was selectively reduced on a platinum catalyst into the di-6-pentacyclo[5.3.0.02,5.03,9.04,8]decylamine. The reaction of reductive dimerization was also characteristic of pentacyclo[4.3.0.02,5.03,8.04,7]-nonan-9-one and pentacyclo[6.3.0.02,6.03,10.05,9]undecan-4-one oximes, whereas the composition of the reduction products of pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-one oxime depended on the amount of the catalyst.

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Authors and Affiliations

  1. National Technical University of Ukraine “Kiev Polytechnic Institute,”, Kiev, 03056, Ukraine

    V. N. Rodionov, A. S. Sklyarova, T. V. Shamota & A. A. Fokin

  2. Justus Liebig Universitaet, Heinrich Baff Ring 58, 35392, Gissen, BRD

    P. R. Schreiner

Authors
  1. V. N. Rodionov
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  2. A. S. Sklyarova
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  3. T. V. Shamota
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  4. P. R. Schreiner
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  5. A. A. Fokin
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Correspondence to V. N. Rodionov.

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Original Russian Text © V.N. Rodionov, A.S. Sklyarova, T.V. Shamota, P.R. Schreiner, A.A. Fokin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 11, pp. 1662–1668.

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Rodionov, V.N., Sklyarova, A.S., Shamota, T.V. et al. Selective reductive dimerization of homocubane series oximes. Russ J Org Chem 47, 1695–1702 (2011). https://doi.org/10.1134/S1070428011110078

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  • DOI: https://doi.org/10.1134/S1070428011110078

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