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Synthesis of fluorinated N-arylpyrazoles with perfluoro-2-methyl-2-pentene and arylhydrazines Full article

Journal Journal of Fluorine Chemistry
ISSN: 0022-1139
Output data Year: 1999, Volume: 98, Number: 1, Pages: 29-36 Pages count : 8 DOI: 10.1016/S0022-1139(99)00079-2
Tags perfluoro-2-methyl-2-pentene; arylhydrazines; pyrazoles; fluorinated N-arylpyrazoles; structure 3-fluoro-5-pentafluoroethyl-1-phenyl-4-trifluoromethylpyrazole
Authors Chi Ki-Whan 1 , Kim Sung-Jun 1 , Park Tae-Ho 2 , Gatilov Yurii V. 3 , Bagryanskaya Irina Yu. 3 , Furin Georgii G. 3
Affiliations
1 Department of Chemistry, University of Ulsan, Ulsan 680-749, South Korea
2 Korea Research Institute of Chemical Technology, Taejeon 305-606, South Korea
3 Institute of Organic Chemistry, Russian Academy of Sciences, 630090, Novosibirsk, Russian Federation

Abstract: Reactions of arylhydrazines (phenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, pentafluorophenyl, 4-trifluoromethyl-2,3,5,6-tetrafluorophenylhydrazine or 4,4'-dihydrazinooctafluorobiphenyl) with perfluoro-2-methyl-2-pentene in the presence of triethylamine have effectively produced 1-aryl-perfluoro-3-ethyl-4-methylpyrazole and 1-aryl-perfluoro-5-ethyl-4-methylpyrazole in various ratios depending on the reaction conditions and arylhydrazine used. Syn- and anti-aminoimines which might be the intermediates for pyrazoles have been isolated under appropriate conditions. The routes of formation for these products and the role of triethylamine have been discussed. The reaction of perfluoro-2-methyl-2-pentene with phenylhydrazine has been investigated in detail. The structure of 3-fluoro-5-pentafluoroethyl-1-phenyl-4-trifluoromethylpyrazole has been elucidated by X-ray crystallography. (C) 1999 Elsevier Science S.A. All rights reserved.
Cite: Chi K-W. , Kim S-J. , Park T-H. , Gatilov Y.V. , Bagryanskaya I.Y. , Furin G.G.
Synthesis of fluorinated N-arylpyrazoles with perfluoro-2-methyl-2-pentene and arylhydrazines
Journal of Fluorine Chemistry. 1999. V.98. N1. P.29-36. DOI: 10.1016/S0022-1139(99)00079-2 WOS Scopus OpenAlex
Dates:
Published print: Aug 1, 1999
Identifiers:
Web of science: WOS:000081577500005
Scopus: 2-s2.0-0033543042
OpenAlex: W1992393200
Citing:
DB Citing
Web of science 14
Scopus 15
OpenAlex 16
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