Conclusions
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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.
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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.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 344–351, February, 1989.
The authors are indebted to R. B. Dmitriev for undertaking the mass-spectrometric analysis of the dicyanogen.
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Troyanskii, É.I., Mizintsev, V.V., Samoshin, V.V. et al. Stereochemistry of the remote oxidative cyanation of methylcyclohexanones. Russ Chem Bull 38, 294–300 (1989). https://doi.org/10.1007/BF00953616
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DOI: https://doi.org/10.1007/BF00953616