Aberrant S(RN)1 Reaction of 4-Aminophenol with alpha,p-Dinitrocumene: EPR Observation of Intermediates.
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.
Scamehorn
RG
Department of Chemistry, Ripon College, Ripon, Wisconsin 54971, and University of St. Andrews, School of Chemistry, St. Andrews, Fife, United Kingdom KY16 9ST.
Mahnke
LA
Krause
RD
Frey
BL
Hendriksen
DL
Jahn
KS
Kultgen
SG
Walton
JC