Selective mono-and diamination of polyfluorinated benzenes and pyridines with liquid ammonia

Selective mono-and diamination of polyfluorinated benzenes and pyridines with liquid ammonia Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2007, Volume: 56, Number: 11, Pages: 2239-2246 Pages count : 8 DOI: 10.1007/s11172-007-0351-2

Tags

organofluorine compounds; ammonia; aminodefluorination; polyfluorodiaminopyridines; polyfluorophenylenediamines; nucleophilic substitution

Authors

Vaganova T.A. ¹ , Kusov S.Z. ¹ , Rodionov V.I. ¹ , Shundrina I.K. ¹ , Malykhin E.V. ^1,2

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation
2	Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

Amination of pentafluoropyridine, 2,3,5,6-tetrafluoropyridine, 4-chlorotetrafluoropyridine, 3,5-dichlorotrifluoropyridine, octafluorotoluene, alpha,alpha,alpha,2,3,5,6-heptafluorotoluene, decafluoro-m-xylene, decafluorobiphenyl, hexafluorobenzene, and pentafluorobenzene with liquid ammonia was investigated. Bis-aminodefluorination temperatures for the majority of substrates were shown to exceed significantly the corresponding temperatures of monoaminodefluorination. The optimal conditions for selective preparation of mono-and diaminopolyfluoro(het)arenes were elucidated. An efficient method for isolation of particular polyfluorophenylenediamines from product mixtures formed in nonselective reactions of pentafluorobenzene and hexafluorobenzene with aqueous ammonia based on complexation with a crown ether is proposed.

Vaganova T.A. , Kusov S.Z. , Rodionov V.I. , Shundrina I.K. , Malykhin E.V.
Selective mono-and diamination of polyfluorinated benzenes and pyridines with liquid ammonia
Russian Chemical Bulletin. 2007. V.56. N11. P.2239-2246. DOI: 10.1007/s11172-007-0351-2 WOS Scopus РИНЦ

Ваганова Т.А. , Кусов С.З. , Родионов В.И. , Шундрина И.К. , Малыхин Е.В.
Селективное моно- и диаминирование полифторированных производных бензола и пиридина жидким аммиаком
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2007. №11. С.2163-2170. РИНЦ

Published print:

Nov 1, 2007

Web of science	WOS:000255257800015
Scopus	2-s2.0-42449102049
Elibrary	13556152
OpenAlex	W2953069547