title: Aberrant S(RN)1 Reaction of 4-Aminophenol with alpha,p-Dinitrocumene: EPR Observation of Intermediates.
abstract: The tert-butoxide-induced substitution of alpha,p-dinitrocumene by 4-aminophenol unexpectedly afforded the N-coupled product, 2-(4-hydroxyanilino)-2-(4-nitrophenyl)propane. EPR observations revealed arylaminyl radical intermediates as well as coupled anion radicals, hence the normal S(RN)1 process may compete with an alternative nonchain reaction pathway.
authors.affiliation: Department of Chemistry, Ripon College, Ripon, Wisconsin 54971, and University of St. Andrews, School of Chemistry, St. Andrews, Fife, United Kingdom KY16 9ST.
authors.initials: RG
authors.lastname: Scamehorn
authors.initials: LA
authors.lastname: Mahnke
authors.initials: RD
authors.lastname: Krause
authors.initials: BL
authors.lastname: Frey
authors.initials: DL
authors.lastname: Hendriksen
authors.initials: KS
authors.lastname: Jahn
authors.initials: SG
authors.lastname: Kultgen
authors.initials: JC
authors.lastname: Walton