Journal of Organic Chemistry p. 2461 - 2465 (1983)
Update date:2022-08-05
Topics:
Bunton, Clifford A.
de Buzzaccarini, Francesco de
Hamed, Fareed H.
Reactions of 2,4-dinitrochloro- or 2,4-dinitrofluorobenzene in microemulsions of hexadecyl(2-hydroxyethyl)dimethylammonium bromide (1), n-octane, and tert-amyl alcohol or 1-butanol, and NaOH give an ether by attack of the alkoxide zwitterion of 1.This ether slowly reacts with OH(-), giving 2,4-dinitrophenoxide ion.These reactions are slower than those in aqueous micelles.A Meisenheimer complex is formed by reaction of 1-chloro-2,4-dinitronaphthalene in these microemulsions and in those containing 1-butanol, and it is slowly converted into the naphtholate ion by attack of OH(-).
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