Mechanism of electron transfer oxidation of 4-substituted 1-benzyl-1,4-dihydronicotinamides

Naoki Takada; Shinohu Itoh; Shunichi Fukuzumi

doi:10.1246/cl.1996.1103

Mechanism of electron transfer oxidation of 4-substituted 1-benzyl-1,4-dihydronicotinamides

Naoki Takada, Shinohu Itoh, Shunichi Fukuzumi

Department of Chemistry & Nanoscience

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

15 Scopus citations

Abstract

Electron transfer oxidation of variously 4-substituted 1-benzyl-1,4-dihydronicotinamides (RBNAH) by [Fe(phen)₃]³⁺ (phen = 1,10-phenanthroline) results in formation of RBNAH^•+, followed by cleavage of the C(4)-H or C(4)-C bond of RBNAH^•+ depending on the substituent R. In particular, the C(4)-C bond cleavage of t-BuBNAH^•+ yields exclusively BNA⁺ and tert-butyl radical (t-Bu^•) which is detected by applying a rapid mixing flow electron spin resonance (ESR) technique.

Original language	English
Pages (from-to)	1103-1104
Number of pages	2
Journal	Chemistry Letters
Issue number	12
DOIs	https://doi.org/10.1246/cl.1996.1103
State	Published - 1996

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title = "Mechanism of electron transfer oxidation of 4-substituted 1-benzyl-1,4-dihydronicotinamides",

abstract = "Electron transfer oxidation of variously 4-substituted 1-benzyl-1,4-dihydronicotinamides (RBNAH) by [Fe(phen)3]3+ (phen = 1,10-phenanthroline) results in formation of RBNAH•+, followed by cleavage of the C(4)-H or C(4)-C bond of RBNAH•+ depending on the substituent R. In particular, the C(4)-C bond cleavage of t-BuBNAH•+ yields exclusively BNA+ and tert-butyl radical (t-Bu•) which is detected by applying a rapid mixing flow electron spin resonance (ESR) technique.",

author = "Naoki Takada and Shinohu Itoh and Shunichi Fukuzumi",

year = "1996",

doi = "10.1246/cl.1996.1103",

language = "English",

pages = "1103--1104",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Oxford University Press",

number = "12",

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T1 - Mechanism of electron transfer oxidation of 4-substituted 1-benzyl-1,4-dihydronicotinamides

AU - Takada, Naoki

AU - Itoh, Shinohu

AU - Fukuzumi, Shunichi

PY - 1996

Y1 - 1996

N2 - Electron transfer oxidation of variously 4-substituted 1-benzyl-1,4-dihydronicotinamides (RBNAH) by [Fe(phen)3]3+ (phen = 1,10-phenanthroline) results in formation of RBNAH•+, followed by cleavage of the C(4)-H or C(4)-C bond of RBNAH•+ depending on the substituent R. In particular, the C(4)-C bond cleavage of t-BuBNAH•+ yields exclusively BNA+ and tert-butyl radical (t-Bu•) which is detected by applying a rapid mixing flow electron spin resonance (ESR) technique.

AB - Electron transfer oxidation of variously 4-substituted 1-benzyl-1,4-dihydronicotinamides (RBNAH) by [Fe(phen)3]3+ (phen = 1,10-phenanthroline) results in formation of RBNAH•+, followed by cleavage of the C(4)-H or C(4)-C bond of RBNAH•+ depending on the substituent R. In particular, the C(4)-C bond cleavage of t-BuBNAH•+ yields exclusively BNA+ and tert-butyl radical (t-Bu•) which is detected by applying a rapid mixing flow electron spin resonance (ESR) technique.

UR - https://www.scopus.com/pages/publications/0001004022

U2 - 10.1246/cl.1996.1103

DO - 10.1246/cl.1996.1103

M3 - Article

AN - SCOPUS:0001004022

SN - 0366-7022

SP - 1103

EP - 1104

JO - Chemistry Letters

JF - Chemistry Letters

IS - 12

ER -

Mechanism of electron transfer oxidation of 4-substituted 1-benzyl-1,4-dihydronicotinamides

Abstract

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