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Mannich Condensation of exo-2,exo-6-Tricyclo[5.2.1.02,6]decan-8-one

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Abstract

Mannich condensation of exo-2,exo-6-tricyclo[5.2.1.02,6]decan-8-one with paraformaldehyde and dimethylamine hydrochloride results in the addition of dimethylaminomethyl fragment at the C9 atom to give the exo-9-isomer. The reaction of exo-9-dimethylaminomethyl-exo-2,exo-6-tricyclo[5.2.1.02,6]decan-8-one with hydroxylamine hydrochloride in alcoholic alkali yields the corresponding Z-oxime which undergoes selective rearrangement into exo-10-dimethylaminomethyl-9-aza-exo-2,exo-6-tricyclo[5.3.1.02,6]undecan-8-one by the action of sulfuric acid in acetonitrile.

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Authors and Affiliations

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

    S. S. Koval'skaya & N. G. Kozlov

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  1. S. S. Koval'skaya
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  2. N. G. Kozlov
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Koval'skaya, S.S., Kozlov, N.G. Mannich Condensation of exo-2,exo-6-Tricyclo[5.2.1.02,6]decan-8-one. Russian Journal of Organic Chemistry 38, 662–664 (2002). https://doi.org/10.1023/A:1019654920983

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