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Anomalous Direction of the Ene Reaction of Pulegone with 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione

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Abstract

The ene reaction of pulegone with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione, apart from the two previously described products, epimeric 1-[(1S,4R)- and 1-[(1R,4R)-4-methyl-2-oxo-1-(prop-1-en-2-yl)cyclohexyl]-4-phenyl-1,2,4-triazolidine-3,5-diones, gave one more isomer, 1-{1-methyl-1-[(4R)-4-methyl-6-oxocyclohex-1-en-1-yl]ethyl}-4-phenyl-1,2,4-triazolidine-3,5-dione. The latter is formed as a result of addition of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione to the Me2C= carbon atom of pulegone (anti-Markovnikov addition) and double bond migration to the six-membered carbocycle.

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Authors and Affiliations

  1. Alekseev Nizny Novgorod State Technical University, ul. Minina 24, Nizhny Novgorod, 603950, Russia

    I. V. Bodrikov, Yu. A. Kurskii, A. A. Chiyanov, A. Yu. Subbotin & Yu. S. Korovnikova

  2. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, ul. Tropinina 49, Nizhny Novgorod, 603137, Russia

    Yu. A. Kurskii

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

    N. G. Kozlov

Authors
  1. I. V. Bodrikov
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  2. Yu. A. Kurskii
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  3. A. A. Chiyanov
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  4. A. Yu. Subbotin
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  5. N. G. Kozlov
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  6. Yu. S. Korovnikova
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Corresponding author

Correspondence to A. A. Chiyanov.

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Original Russian Text © I.V. Bodrikov, Yu.A. Kurskii, A.A. Chiyanov, A.Yu. Subbotin, N.G. Kozlov, Yu.S. Korovnikova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 9, pp. 1412–1413.

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Bodrikov, I.V., Kurskii, Y.A., Chiyanov, A.A. et al. Anomalous Direction of the Ene Reaction of Pulegone with 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione. Russ J Org Chem 54, 1430–1431 (2018). https://doi.org/10.1134/S1070428018090294

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  • DOI: https://doi.org/10.1134/S1070428018090294

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