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Reductive activation of arenes: XIX. Mechanism and some synthetic applications of the alkylation of phthalodinitrile radical anion

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Abstract

Using cyclopropylmethyl bromide as mechanism-sensitive reagent, it was shown that the reaction of phthalonitrile radical anion with alkyl halides in liquid ammonia involves electron transfer. The effects of the nature of alkyl bromide and counterion in the radical anion salt and reaction conditions on the ratio of 2-alkyl-benzonitrile, 4-alkylphthalonitrile, and 2,5-dialkylbenzonitrile were studied. Phthalodinitrile radical anion was found to undergo dimerization with formation of biphenyl-2,3′,4′-tricarbonitrile. The examined transformations may underlie syntheses of phthalonitriles modified at the 4-position.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    E. V. Panteleeva, T. A. Vaganova & V. D. Shteingarts

  2. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    E. V. Panteleeva & V. D. Shteingarts

  3. “Research Institute of Organic Intermediate Products and Dyes” State Research Center, Moscow, Russia

    E. A. Luk’yanets

Authors
  1. E. V. Panteleeva
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  2. T. A. Vaganova
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  3. E. A. Luk’yanets
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  4. V. D. Shteingarts
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Additional information

Original Russian Text © E.V. Panteleeva, T.A. Vaganova, E.A. Luk’yanets, V.D. Shteingarts, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1301–1309.

For communication XVIII, see [1].

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Panteleeva, E.V., Vaganova, T.A., Luk’yanets, E.A. et al. Reductive activation of arenes: XIX. Mechanism and some synthetic applications of the alkylation of phthalodinitrile radical anion. Russ J Org Chem 42, 1280–1288 (2006). https://doi.org/10.1134/S1070428006090053

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  • DOI: https://doi.org/10.1134/S1070428006090053

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