Aminodefluorination of 2-X-pentafluoro-1,4-naphthoquinones (X = (NHBu)-Bu-n, NEt2, and OMe)

Aminodefluorination of 2-X-pentafluoro-1,4-naphthoquinones (X = (NHBu)-Bu-n, NEt2, and OMe) Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2010, Volume: 131, Number: 1, Pages: 70-77 Pages count : DOI: 10.1016/j.jfluchem.2009.10.007

Tags

Hexafluoro-1,4-naphthoquinone; 2-Alkylaminopentafluoro-1,4-naphthoquinone; Aminodefluorination; Nucleophilic substitution; Regioselectivity

Authors

Troshkova Nadezhda M. ¹ , Goryunov Leonid I. ¹ , Gatilov Yurij V. ¹ , Nevinsky Georgy A. ² , Shteingarts Vitalij D. ^1,3

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Inst Biol Chem Fundamental Med, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

Aminodefluorination of 2-n-butylamino- and 2-diethylaminopentafluoro-1,4-naphthoquinone by alkylamines (HNRR2)-R-1 ((NRR2)-R-1 = NHEt, (NHBu)-Bu-n and NEt2) occurs at the 6- or 8-position and further, accordingly, at the 8- or at one of the 5- and 6-sites. The isomer ratio changes significantly in favor of a beta-replacement product with solvent variation in the sequence: toluene < 1,4-dioxane < DMSO. n-Butylaminodefluorination of 2-methoxypentafluoro-1,4-naphthoquinone gives mixtures of fluorine substitution products both on the benzene and quinone rings. (C) 2009 Elsevier B.V. All rights reserved.

Troshkova N.M. , Goryunov L.I. , Gatilov Y.V. , Nevinsky G.A. , Shteingarts V.D.
Aminodefluorination of 2-X-pentafluoro-1,4-naphthoquinones (X = (NHBu)-Bu-n, NEt2, and OMe)
Journal of Fluorine Chemistry. 2010. V.131. N1. P.70-77. DOI: 10.1016/j.jfluchem.2009.10.007 WOS Scopus РИНЦ

Published print:

Jan 1, 2010

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