Synthesis of 4 '-alkyl-[1,1 '-biphenyl]-2,3 '-dicarbonitriles via dimerisation of phthalonitrile radical anion in liquid ammonia

Synthesis of 4 '-alkyl-[1,1 '-biphenyl]-2,3 '-dicarbonitriles via dimerisation of phthalonitrile radical anion in liquid ammonia Full article

Journal

ARKIVOC
ISSN: 1551-7004 , E-ISSN: 1551-7012

Output data

Year: 2018, Pages: 349-356 Pages count : 8 DOI: 10.24820/ark.5550190.p010.764

Tags

Phthalonitrile; radical anions; dimerisation; reductive alkylation; biphenyl-2,3 '-dicarbonitriles

Authors

Peshkov Roman Yu ^1,2 , Wang Chunyan ^2,3 , Panteleeva Elena, V ^1,2 , Tretyakov Evgeny, V ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova St, Novosibirsk 630090, Russia
3	(Данные Web of science) Heilongjang Univ, Xuefu Rd 74, Harbin 150080, Heilongjiang, Peoples R China

Single-electron reduction of phthalonitrile by metallic lithium in liquid ammonia resulted in a radical anion salt that underwent dimerisation yielding a long-lived intermediate, the 1,2-dicyano-4-(2-cyanophenyl)cyclohexa-2,5-dienyl anion. Alkylation of this anion with primary alkyl iodides resulted in a convenient one-pot synthesis of 4'-alkyl-[1,1'-biphenyl]-2,3'-dicarbonitriles. [GRAPHICS] .

Peshkov R.Y. , Wang C. , Panteleeva E.V. , Tretyakov E.V.
Synthesis of 4 '-alkyl-[1,1 '-biphenyl]-2,3 '-dicarbonitriles via dimerisation of phthalonitrile radical anion in liquid ammonia

ARKIVOC. 2018. P.349-356. DOI: 10.24820/ark.5550190.p010.764 WOS Scopus РИНЦ

Full text from publisher

Published online:

Nov 25, 2018

Web of science	WOS:000456187500030
Scopus	2-s2.0-85058940519
Elibrary	38653792
OpenAlex	W2923880450