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Reaction of Tetracyanoethylene with 2-Substituted Cyclohexanones

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Abstract

Reactions of 2-methylcyclohexanone and menthone with tetracyanoethylene gave 2-(1,1,2,2-tetracyanoethyl)cyclohexanones which underwent quantitative transformation in the solid phase into 3,4-cyanosubstituted 2-aminopyrans in 2-3 days at room temperature. 2-Methyl-2-(1,1,2,2-tetracyanoethyl)cyclohexanone reacted with hydroiodic acid to afford 8a-hydroxy-2-iodo-4a-methyl-1,4,4a,5,6,7,8,8a-octahydroquinoline-3,4,4-tricarbonitrile. The reaction of 2,2'-methylenedi(cyclohexanone) with tetracyanoethylene resulted in formation of 7-imino-4,5-tetramethylene-2'-oxo-6-oxabicyclo[3.2.1]octane-2-spiro-1'-cyclohexane-1,8,8-tricarbonitrile.

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  1. Ul'yanov Chuvash State University, Moskovskii pr. 15, Cheboksary, 428015, Russia

    V. P. Sheverdov, O. V. Ershov, O. E. Nasakin, A. N. Chernushkin & V. A. Tafeenko

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  1. V. P. Sheverdov
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  2. O. V. Ershov
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  3. O. E. Nasakin
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  4. A. N. Chernushkin
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  5. V. A. Tafeenko
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Sheverdov, V.P., Ershov, O.V., Nasakin, O.E. et al. Reaction of Tetracyanoethylene with 2-Substituted Cyclohexanones. Russian Journal of Organic Chemistry 38, 1001–1004 (2002). https://doi.org/10.1023/A:1020801612443

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  • DOI: https://doi.org/10.1023/A:1020801612443

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