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

Aberrant S_RN1 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

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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 S_RN1 process may compete with an alternative nonchain reaction pathway.

Original language	English
Pages (from-to)	827-829
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	6
Publication status	Published - 23 Mar 2000

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

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.",

author = "Scamehorn, {Richard G.} and Mahnke, {Lisa A.} and Krause, {Renee D.} and Frey, {Brian L.} and Hendriksen, {Deborah L.} and Jahn, {Kelly S.} and Kultgen, {Steven G.} and Walton, {John C.}",

year = "2000",

month = mar,

day = "23",

language = "English",

volume = "2",

pages = "827--829",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "6",

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TY - JOUR

T1 - Aberrant SRN1 reaction of 4-aminophenol with α,p-dinitrocumene

T2 - EPR observation of intermediates

AU - Scamehorn, Richard G.

AU - Mahnke, Lisa A.

AU - Krause, Renee D.

AU - Frey, Brian L.

AU - Hendriksen, Deborah L.

AU - Jahn, Kelly S.

AU - Kultgen, Steven G.

AU - Walton, John C.

PY - 2000/3/23

Y1 - 2000/3/23

N2 - (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.

AB - (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.

UR - http://www.scopus.com/inward/record.url?scp=0001211082&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0001211082

SN - 1523-7060

VL - 2

SP - 827

EP - 829

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Aberrant S_RN1 reaction of 4-aminophenol with α,p-dinitrocumene: EPR observation of intermediates

Abstract

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