Aberrant S(RN)1 reaction of 4-aminophenol with alpha,p-dinitrocumene: EPR observation of intermediates

Authors
Scamehorn, RG Mahnke, LA Krause, RD Frey, BL Hendriksen, DL Jahn, KS Kultgen, SG Walton, JC
Citation
Rg. Scamehorn et al., Aberrant S(RN)1 reaction of 4-aminophenol with alpha,p-dinitrocumene: EPR observation of intermediates, ORG LETT, 2(6), 2000, pp. 827-829
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
6
Year of publication
2000
Pages
827 - 829
Database
ISI
SICI code
1523-7060(20000323)2:6<827:ASRO4W>2.0.ZU;2-U
Abstract
The tert-butoxide-induced substitution of alpha,p-dinitrocumene by 4-aminop henol unexpectedly afforded the N-coupled product, 2-(4-hydroxyanilino)-2-( 4-nitrophenyl)propane. EPR observations revealed arylaminyl radical interme diates as well as coupled anion radicals, hence the normal S(RN)1 process m ay compete with an alternative nonchain reaction pathway.