Reductive activation of arenes. XII. Reaction of the product of phthalonitrile one-electron reduction with butyl halides in liquid ammonia

Reductive activation of arenes. XII. Reaction of the product of phthalonitrile one-electron reduction with butyl halides in liquid ammonia Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 1998, Volume: 34, Number: 11, Pages: 1632-1639 Pages count : 8

Authors

Panteleeva E.V. ¹ , Bilkis I.I. ² , Steingarts V.D. ¹

Affiliations

1	(Scopus) Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russian Federation
2	(Scopus) Faculty of Agriculture, Hebrew University of Jerusalem, Israel

The product of one-electron reduction of the phthalonitrile with metallic potassium in liquid ammonia reacts with butyl halides (BuCl, BuBr, BuI, s-BuBr, t-BuBr, t-BuI) to yield compounds of alkyl bonding in ipso(2-butylbenzonitriles) and unsubstituted (4-butyl-1,2-dicyanobenzenes and 2,5-dibutylbenzonitriles) positions of the aromatic ring of the original dinitrile. The dependence of the product composition on the character of alkyl moiety and halogen atom in the butyl halide is rationalized by reaction mechanism including at the first stage electron transfer from the anion-radical of the phthalonitrile to the alkyl halide and followed by recombination of the alkyl radical produced with another molecule of anionradical. © 1998 MAHK" Hayka/Interperiodica".

Panteleeva E.V. , Bilkis I.I. , Steingarts V.D.
Reductive activation of arenes. XII. Reaction of the product of phthalonitrile one-electron reduction with butyl halides in liquid ammonia
Russian Journal of Organic Chemistry. 1998. V.34. N11. P.1632-1639. Scopus РИНЦ

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