Aberrant SRN1 Reaction of 4-Aminophenol with ,p-Dinitrocumene: EPR Observation of Intermediates

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• 作者：Richard G. Scamehorn ; Lisa A. Mahnke ; Renee D. Krause ; Brian L. Frey ; Deborah L. Hendriksen ; Kelly S. Jahn ; Steven G. Kultgen ; and John C. Walton
• 刊名：Organic Letters
• 出版年：2000
• 出版时间：March 23, 2000
• 年：2000
• 卷：2
• 期：6
• 页码：827 - 829
• 全文大小：54K
• 年卷期：v.2,no.6(March 23, 2000)
• ISSN：1523-7052

文摘

The tert-butoxide-induced substitution of ,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 normalS_RN1 process may compete with an alternative nonchain reaction pathway.

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