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Formation of isoindole derivatives by reaction of phthalonitrile with sodium methoxide

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown by means of IR spectra that the reaction of phthalonitrile with sodium methoxide in benzene in the presence of traces of water or methanol proceeds via a series-parallel mechanism in two steps to give cyclic products. The proposed structure of the intermediate is an oligomeric isbindolenine chain with terminal NNa and OCH3 groups. The final product is the sodium salt of monomethoxyiminoisoindolenine. The analogous reaction in methanol proceeds at a higher rate that makes it impossible to isolate or detect the intermediate; the final product is 1,1-dimethoxy-3-iminoisoindoline.

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Authors and Affiliations

  1. Scientific-Research Institute of Organic Intermediates and Dyes, 103787, Moscow

    É. V. Pankratova, G. N. Rodionova, B. E. Zaitsev & V. A. Titkov

Authors
  1. É. V. Pankratova
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  2. G. N. Rodionova
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  3. B. E. Zaitsev
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  4. V. A. Titkov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 63–68., January, 1977.

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Pankratova, É.V., Rodionova, G.N., Zaitsev, B.E. et al. Formation of isoindole derivatives by reaction of phthalonitrile with sodium methoxide. Chem Heterocycl Compd 13, 54–58 (1977). https://doi.org/10.1007/BF00479869

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  • DOI: https://doi.org/10.1007/BF00479869

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