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.
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Aberrant S(RN)1 Reaction of 4-Aminophenol with alpha,p-Dinitrocumene: EPR Observation of Intermediates.
Org Lett
March 2000
Department of Chemistry, Ripon College, Ripon, Wisconsin 54971, and University of St. Andrews, School of Chemistry, St. Andrews, Fife, United Kingdom KY16 9ST.
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.
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