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Decarboxylation in proton acceptor solvents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Heating 3,8-dinitro-10-carboxy-6H-dibenzo[b,d]pyran-6-one in DMSO, DMF, or HMPTA leads to decarboxylation and the replacement of the carboxyl group by a hydroxy group with the formation of 3,8-dinitro-6H-dibenzo[b,d]pyran-6-one and 3,8-dinitro-10-hydroxy-6H-dibenzo [b,d]pyran-6-one. The decarboxylation of 2,7-dinitro-5,10-dioxo-4,5,9,10-tetrahydro-4,9-dioxapyrene in HMPTA is preceded by opening of the two lactone rings and the formation of a 1:4 molecular complex of 4,4′-dinitro-6,6′-dihydroxy-2,2′-dicarboxybiphenyl with HMPTA, whose structure was established by x-ray diffraction structural analysis.

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Authors and Affiliations

  1. Research Institute for Organic Intermediates and Dyes, 103787, Moscow

    A. M. Andrievskii, A. N. Poplavskii, N. G. Grekhova, K. M. Dyumaev, E. G. Popova, A. N. Sobolev, L. A. Chetkina & V. K. Bel'skii

  2. L. Ya. Karpov Physical Chemistry Research Institute, 107120, Moscow

    A. M. Andrievskii, A. N. Poplavskii, N. G. Grekhova, K. M. Dyumaev, E. G. Popova, A. N. Sobolev, L. A. Chetkina & V. K. Bel'skii

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  1. A. M. Andrievskii
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  2. A. N. Poplavskii
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  3. N. G. Grekhova
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  4. K. M. Dyumaev
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  5. E. G. Popova
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  6. A. N. Sobolev
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  7. L. A. Chetkina
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  8. V. K. Bel'skii
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Additional information

Translated from Khimiya Geterotsiklicheskik Soedinenii, No. 2, pp. 164–170, February, 1989.

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Andrievskii, A.M., Poplavskii, A.N., Grekhova, N.G. et al. Decarboxylation in proton acceptor solvents. Chem Heterocycl Compd 25, 128–133 (1989). https://doi.org/10.1007/BF00479903

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  • DOI: https://doi.org/10.1007/BF00479903

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