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Synthesis, acid-base properties, and deselenation of 5,6,8,9,11,12-hexakis(4-tert-butylphenyl)[1,2,5]selenadiazolo[3,4-b]porphyrazine

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Abstract

Cross cyclotetramerization of bis(4-tert-butylphenyl)fumaronitrile with 1,2,5-selenadiazole-3,4-dicarbonitrile in the presence of magnesium butoxide as template afforded a mixture of magnesium(II) porphyrazine complexes, from which magnesium complex of 5,6,8,9,11,12-hexakis(4-tert-butylphenyl)[1,2,5]selenadiazolo[3,4-b]porphyrazine was isolated by column chromatography and was subjected to demetalation on treatment with trifluoroacetic acid. The free ligand was found to undergo protonation at one meso-nitrogen atom in acid medium and deprotonation of one pyrrole ring to form monoanion by the action of bases. Reductive deselenation of the title compound with formation of vicinal diamino porphyrazine was studied by spectral and kinetic methods, and a mechanism involving two hydrosulfide ions was proposed.

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Authors and Affiliations

  1. Ivanovo State University of Chemistry and Technology, pr. F. Engel’sa 7, Ivanovo, 153000, Russia

    A. V. Kozlov & P. A. Stuzhin

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  1. A. V. Kozlov
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  2. P. A. Stuzhin
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Correspondence to P. A. Stuzhin.

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Original Russian Text © A.V. Kozlov, P.A. Stuzhin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 6, pp. 928–935.

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Kozlov, A.V., Stuzhin, P.A. Synthesis, acid-base properties, and deselenation of 5,6,8,9,11,12-hexakis(4-tert-butylphenyl)[1,2,5]selenadiazolo[3,4-b]porphyrazine. Russ J Org Chem 49, 913–921 (2013). https://doi.org/10.1134/S1070428013060195

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