REACTIONS OF RADICALS GENERATED FROM 1-ETHYL-1,4-DIAZINIUM SALTS: ADDITION TO THE C-C TRIPLE BOND VERSUS DIMERIZATION / Rusinov Gennadiy L.,Verbitskiy Egor V.,Slepukhin Pavel A.,Zabelina Olga N.,Kodess Mikhail I.,Ezhikova Marina A.,Charushin Valeriy N.,Chupakhin Oleg N. // HETEROCYCLES. - 2009. - V. 78, l. 9. - P. 2315-2324.

ISSN/EISSN:

0385-5414 / 1881-0942

Type:

Article

Abstract:

Radical species generated from 5-aryl-substituted 1-ethyl-2,3-dicyano-1,4-diazinium salts by action of sodium iodide undergo dimerization into {[}2,2']bipyrazinyl derivatives, as evidenced by NMR and X-ray crystallography data. The pyrazinyl radicals can also be involved into the addition reaction on the C-C triple bond, thus demonstrating a new synthetic route to modify the structure of pyrazines. The structures of E- and Z-isomers of 1-(1',2'-dihydropyrazinyl-2')-2-iodoethenes have been proved by H-1 and C-13 NMR spectroscopy and X-ray analysis.

Author keywords:

Diazinium Salt; Radical; Arylacetylene; C-C Coupling; Pyrazine O-NUCLEOPHILES; ALKYNES; ACETYLENES; ALKENES; 1,2,4-TRIAZINES; SUBSTITUTION; HYDROGEN; CATION

DOI:

10.3987/COM-09-11734

Web of Science ID:

ISI:000270639900011

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	SEP 1
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
EISSN	1881-0942
Keywords-Plus	O-NUCLEOPHILES; ALKYNES; ACETYLENES; ALKENES; 1,2,4-TRIAZINES; SUBSTITUTION; HYDROGEN; CATION
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	Rusinov@ios.uran.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}07-03-12112-ofi, 07-03-96113-r\_ural\_a, and 07-03-96123-r\_ural\_a]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (grants no. 07-03-12112-ofi, 07-03-96113-r\_ural\_a, and 07-03-96123-r\_ural\_a), the State Program for Supporting of Leading Scientific Schools of the Russian Federation (grants NSh 3758.2008.3 and NSh 3257.2008.2) and the Program of Presidium RAS X211). We thank to Dr. Yuriy N. Shvachko and Mr. Denis V. Starichenko from the Institute of Metal Physics (Ekaterinburg, Russia) for recording ESR spectra.
Number-of-Cited-References	31
Usage-Count-Since-2013	5
Journal-ISO	Heterocycles
Doc-Delivery-Number	504TF