Aberrant SRN1 reaction of 4-aminophenol with α,p-dinitrocumene: EPR observation of intermediates

Richard G. Scamehorn*, Lisa A. Mahnke, Renee D. Krause, Brian L. Frey, Deborah L. Hendriksen, Kelly S. Jahn, Steven G. Kultgen, John C. Walton

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

(figure presented) The tert-butoxide-induced substitution of α,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 SRN1 process may compete with an alternative nonchain reaction pathway.

Original languageEnglish
Pages (from-to)827-829
Number of pages3
JournalOrganic Letters
Volume2
Issue number6
Publication statusPublished - 23 Mar 2000

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