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Stereochemistry of the remote oxidative cyanation of methylcyclohexanones

  • É. I. Troyanskii
  • V. V. Mizintsev
  • V. V. Samoshin
  • A. I. Lutsenko
  • V. A. Svyatkin
  • G. I. Nikishin
Orgamic Chemistry

Conclusions

  1. 1.

    During the oxidative cyanation of 2-, 3-, and 4-methylcyclohexanones in the Na2S2O8-NaCN system the corresponding 4-cyano(methyl)cyclohexanones are formed regiospecifically.

     
  2. 2.

    The oxidative cyanation of 2- and 3-methylcyclohexanones takes place diastereoselectively with the formation of trans- and cis-4-cyano-2(3)-methylcyclohexanones in a ratio of 1.5∶1 (or 2∶1). The selectivity of cyanation is determined by the bridge structure of the intermediate 4-oxo(methyl)cyclohexyl radicals, which are the precursors of the 4-cyanocyclohexanones.

     

Keywords

Methyl Cyclohexanone Cyclohexyl Bridge Structure Methylcyclohexanones 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • É. I. Troyanskii
    • 1
  • V. V. Mizintsev
    • 1
  • V. V. Samoshin
    • 1
  • A. I. Lutsenko
    • 1
  • V. A. Svyatkin
    • 1
  • G. I. Nikishin
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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