Abstract: Monoamination of octafluoronaphthalene by liquid ammonia affords 2-aminoheptafluoronaphthalene mainly (isolated yield 85-90%). Diamination of octafluoronaphthalene or amination of 2-aminoheptafluoronaphthalene affords a mixture of isomeric 1,6-, 1,7-, 2,6-, and 2,7-diaminohexafluoronaphthalenes with considerable prevalence of the 2,7-isomer (similar to 70%), thus being the first example of the predominant substitution at position 7 in 2-substituted polyfluoronaphthalenes. The 2,7/2,6 ratio of 2-X-heptafluoronaphthalene (X = -NH, NH2 and NHAc) amination diminishes with the decrease of electron-donating effect of the substituent; 2,7-diaminohexafluoronaphthalene forms in the reactions of 2-aminoheptafluoronaphthalene or octafluoronaphthalene with excess of NaNH2 in liquid ammonia and 2,6-diaminohexafluoronaphthalene-in the reaction of 2-acetylamidoheptafluoronaphthalene with liquid ammonia followed by acetylamido group hydrolysis. The method of the selective preparation of these diamines based on the reversible transformation of amino group and a convenient technique of their high purity isolation by complexation with crown ether have been elaborated. (C) 2007 Elsevier B.V. All rights reserved.

Cite: Vaganova T.A. , Kusov S.Z. , Rodionov V.I. , Shundrina I.K. , Sal'nikov G.E. , Mamatyuk V.I. , Malykhin E.V.
Amination of octafluoronaphthalene in liquid ammonia 2,6- and 2,7-diaminohexafluoronaphthalenes selective preparation
Journal of Fluorine Chemistry. 2008. V.129. N4. P.253-260. DOI: 10.1016/j.jfluchem.2007.11.010 WOS Scopus РИНЦ

Dates:

Published print:

Apr 1, 2008

Identifiers:

Web of science	WOS:000255109300003
Scopus	2-s2.0-40649107150
Elibrary	13566095
OpenAlex	W1975192826

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