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Mannich Condensation of 3,3,5-Trimethylcyclohexanone and Its Oxime

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Abstract

Mannich condensation of 3,3,5-trimethylcyclohexanone with paraformaldehyde and dimethylamine or benzylamine hydrochloride involves both activated methylene group in the initial ketone to give compounds with equatorial aminomethyl substituent. The major isomer is that formed by addition at the less sterically hindered carbon atom. Likewise, Mannich condensation of the E and Z isomers of 3,3,5-trimethylcyclohexanone oxime react at both methylene groups, and the addition of aminomethyl fragment occurs preferentially at that methylene group which is located more closely to the oxime hydroxy group.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    S. S. Koval'skaya & N. G. Kozlov

  2. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent'eva 9, Novosibirsk, 630090, Russia

    A. V. Tkachev

Authors
  1. S. S. Koval'skaya
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  2. N. G. Kozlov
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  3. A. V. Tkachev
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 12, 2005, pp. 1869–1878.

Original Russian Text Copyright © 2005 by Koval'skaya, Kozlov, Tkachev.

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Koval'skaya, S.S., Kozlov, N.G. & Tkachev, A.V. Mannich Condensation of 3,3,5-Trimethylcyclohexanone and Its Oxime. Russ J Org Chem 41, 1836–1844 (2005). https://doi.org/10.1007/s11178-006-0045-5

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  • DOI: https://doi.org/10.1007/s11178-006-0045-5

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