Nucleophilic Aromatic Substitution in Microemulsions of a Hydroxyethyl Surfactant

Article abstract of DOI:10.1021/jo00163a004

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(-).