Aberrant S(RN)1 Reaction of 4-Aminophenol with alpha,p-Dinitrocumene: EPR Observation of Intermediates

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 m...

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Veröffentlicht in:Organic letters 2000-03, Vol.2 (6), p.827-829
Hauptverfasser: Scamehorn, RG, Mahnke, LA, Krause, RD, Frey, BL, Hendriksen, DL, Jahn, KS, Kultgen, SG, Walton, JC
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7052
DOI:10.1021/ol005573v