Abstract: Using cyclopropylmethyl bromide as mechanism-sensitive reagent, it was shown that the reaction of phthalonitrile radical anion with alkyl halides in liquid ammonia involves electron transfer. The effects of the nature of alkyl bromide and counterion in the radical anion salt and reaction conditions on the ratio of 2-alkylbenzonitrile, 4-alkylphthalonitrile, and 2,5-dialkylbenzonitrile were studied. Phthalodinitrile radical anion was found to undergo dimerization with formation of biphenyl-2,'3',4'-tricarbonitrile. The examined transformations may underlie syntheses of phthalonitriles modified at the 4-position.

Cite: Panteleeva E.V. , Vaganova T.A. , Luk'yanets E.A. , Shteingarts V.D.
Reductive activation of arenes: XIX. Mechanism and some synthetic applications of the alkylation of phthalodinitrile radical anion
Russian Journal of Organic Chemistry. 2006. V.42. N9. P.1280-1288. DOI: 10.1134/S1070428006090053 WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Пантелеева Е.В. , Ваганова Т.А. , Лукьянец Е.А. , Штейнгарц В.Д.
Восстановительная активация аренов xix/ механизм и некоторые синтетические приложения алкилирования анион-радикала фталодинитрила
Журнал органической химии (RUSS J ORG CHEM+). 2006. Т.42. №9. С.1301-1309. РИНЦ

Dates:

Published print:

Sep 1, 2006

Identifiers:

Web of science	WOS:000241615500005
Scopus	2-s2.0-33750001163
Elibrary	13519640
OpenAlex	W1971277993

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