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

RG Scamehorn; LA Mahnke; RD Krause; BL Frey; DL Hendriksen; KS Jahn; SG Kultgen; John Christopher Walton

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

RG Scamehorn, LA Mahnke, RD Krause, BL Frey, DL Hendriksen, KS Jahn, SG Kultgen, John Christopher Walton

Research output: Other contribution

Abstract

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.

Original language	English
Volume	2
Publication status	Published - 23 Mar 2000

Keywords

AROMATIC NUCLEOPHILIC-SUBSTITUTION
ELECTRON-TRANSFER
ANION
MECHANISM
RADICALS
PROCEED
SYSTEM

Cite this

@misc{1dd621fa2d63440594dee9f0996fab4e,

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

abstract = "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.",

keywords = "AROMATIC NUCLEOPHILIC-SUBSTITUTION, ELECTRON-TRANSFER, ANION, MECHANISM, RADICALS, PROCEED, SYSTEM",

author = "RG Scamehorn and LA Mahnke and RD Krause and BL Frey and DL Hendriksen and KS Jahn and SG Kultgen and Walton, \{John Christopher\}",

note = "Org Lett",

year = "2000",

month = mar,

day = "23",

language = "English",

volume = "2",

type = "Other",

}

TY - GEN

T1 - Aberrant SRN1 reaction of 4-aminophenol with a,p-dinitrocumene: EPR observation of intermediates

AU - Scamehorn, RG

AU - Mahnke, LA

AU - Krause, RD

AU - Frey, BL

AU - Hendriksen, DL

AU - Jahn, KS

AU - Kultgen, SG

AU - Walton, John Christopher

N1 - Org Lett

PY - 2000/3/23

Y1 - 2000/3/23

N2 - 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.

AB - 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.

KW - AROMATIC NUCLEOPHILIC-SUBSTITUTION

KW - ELECTRON-TRANSFER

KW - ANION

KW - MECHANISM

KW - RADICALS

KW - PROCEED

KW - SYSTEM

M3 - Other contribution

VL - 2

ER -

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

Abstract

Keywords

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