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Radical Intermediates of Nucleophilic Addition of Pyrroles to Disubstituted Activated Acetylenes

Radical Intermediates of Nucleophilic Addition of Pyrroles to Disubstituted Activated Acetylenes Doklady Chemistry, Vol. 390, Nos. 4–6, 2003, pp. 137–140. Translated from Doklady Akademii Nauk, Vol. 390, No. 4, 2003, pp. 484–487. Original Russian Text Copyright © 2003 by Vakul’skaya, Sobenina, Mikhaleva, Elokhina, Mal’kina, Trofimov. CHEMISTRY Radical Intermediates of Nucleophilic Addition of Pyrroles to Disubstituted Activated Acetylenes T. I. Vakul’skaya, L. N. Sobenina, A. I. Mikhaleva, V. N. Elokhina, A. G. Mal’kina, and Academician B. A. Trofimov Received February 27, 2003 Electron transfer is the most important elementary step in many chemical transformations [1]. Interest in CN this phenomenon is progressively increasing [2]. How- 1 (4) ever, its role in the reactions of nucleophilic addition to a triple bond is still unclear. Our studies in this field [3– (1Ð3) 7] indicate that this role is much larger than has hitherto 2 2 been supposed. Studying the mechanism of pyrrole addition to acet- N N ylenes catalyzed by the KOH–DMSO superbasic sys- CN tem, we detected by EPR [3–5] the formation of pyrro- CN lyl radicals and radicals resulting from the reaction of (1àÐ3à) pyrrole (1) with phenylcyanoacetylene (4). The EPR 1 2 1 2 1 2 R = R = H (1, 1a); R = Ph, R = H (2, http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Doklady Chemistry Springer Journals

Radical Intermediates of Nucleophilic Addition of Pyrroles to Disubstituted Activated Acetylenes

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References (2)

Publisher
Springer Journals
Copyright
Copyright © 2003 by MAIK “Nauka/Interperiodica”
Subject
Chemistry; Chemistry/Food Science, general; Industrial Chemistry/Chemical Engineering
ISSN
0012-5008
eISSN
1608-3113
DOI
10.1023/A:1024407006228
Publisher site
See Article on Publisher Site

Abstract

Doklady Chemistry, Vol. 390, Nos. 4–6, 2003, pp. 137–140. Translated from Doklady Akademii Nauk, Vol. 390, No. 4, 2003, pp. 484–487. Original Russian Text Copyright © 2003 by Vakul’skaya, Sobenina, Mikhaleva, Elokhina, Mal’kina, Trofimov. CHEMISTRY Radical Intermediates of Nucleophilic Addition of Pyrroles to Disubstituted Activated Acetylenes T. I. Vakul’skaya, L. N. Sobenina, A. I. Mikhaleva, V. N. Elokhina, A. G. Mal’kina, and Academician B. A. Trofimov Received February 27, 2003 Electron transfer is the most important elementary step in many chemical transformations [1]. Interest in CN this phenomenon is progressively increasing [2]. How- 1 (4) ever, its role in the reactions of nucleophilic addition to a triple bond is still unclear. Our studies in this field [3– (1Ð3) 7] indicate that this role is much larger than has hitherto 2 2 been supposed. Studying the mechanism of pyrrole addition to acet- N N ylenes catalyzed by the KOH–DMSO superbasic sys- CN tem, we detected by EPR [3–5] the formation of pyrro- CN lyl radicals and radicals resulting from the reaction of (1àÐ3à) pyrrole (1) with phenylcyanoacetylene (4). The EPR 1 2 1 2 1 2 R = R = H (1, 1a); R = Ph, R = H (2,

Journal

Doklady ChemistrySpringer Journals

Published: Oct 17, 2004

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