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
Publication type: Journal Article
Publication date: 2013-06-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
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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A.V. K., 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 // Russian Journal of Organic Chemistry. 2013. Vol. 49. No. 6. pp. 913-921.
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A.V. K., 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 // Russian Journal of Organic Chemistry. 2013. Vol. 49. No. 6. pp. 913-921.
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TY - JOUR
DO - 10.1134/S1070428013060195
UR - https://doi.org/10.1134/S1070428013060195
TI - 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
T2 - Russian Journal of Organic Chemistry
AU - A.V., Kozlov
AU - Stuzhin, P A
PY - 2013
DA - 2013/06/01
PB - Pleiades Publishing
SP - 913-921
IS - 6
VL - 49
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2013_A.V.,
author = {Kozlov A.V. and P A Stuzhin},
title = {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},
journal = {Russian Journal of Organic Chemistry},
year = {2013},
volume = {49},
publisher = {Pleiades Publishing},
month = {jun},
url = {https://doi.org/10.1134/S1070428013060195},
number = {6},
pages = {913--921},
doi = {10.1134/S1070428013060195}
}
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A.V., Kozlov, and P A Stuzhin. “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.” Russian Journal of Organic Chemistry, vol. 49, no. 6, Jun. 2013, pp. 913-921. https://doi.org/10.1134/S1070428013060195.
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