Cation pool method based on C-C bond dissociation. Effective generation of monocations and dications

被引：65

作者：

Okajima, M ^{[1
]}

Suga, S ^{[1
]}

Itami, K ^{[1
]}

Yoshida, J ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 19期

关键词：

D O I：

10.1021/ja050414y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The "cation pools" of alkoxyarylcarbenium ions were effectively generated by the oxidative C-C bond dissociation using low temperature electrolysis. The present method is especially effective for the generation and accumulation of dications, which react with carbon nucleophiles. Copyright © 2005 American Chemical Society.

引用

页码：6930 / 6931

页数：2

共 41 条

[1] Catalytic aerobic generation of acyliminium ions through electron-transfer-mediated carbon-carbon bond activation [J].

Aubele, DL ;

Rech, JC ;

Floreancig, PE .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :359-366

[2] Side-chain fragmentation of arylalkanol radical cations. Carbon-carbon and carbon-hydrogen bond cleavage and the role of alpha- and beta-OH groups [J].

Baciocchi, E ;

Bietti, M ;

Putignani, L ;

Steenken, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) :5952-5960

[3] Mechanistic aspects of β-bond-cleavage reactions of aromatic radical cations [J].

Baciocchi, E ;

Bietti, M ;

Lanzalunga, O .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (04) :243-251

[4] CARBON-HYDROGEN VS CARBON-CARBON BOND-CLEAVAGE OF 1,2-DIARYLETHANE RADICAL CATIONS IN ACETONITRILE-WATER [J].

CAMAIONI, DM ;

FRANZ, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1607-1613

[5] CALCULATION OF STRUCTURES AND BOND-DISSOCIATION ENERGIES OF RADICAL CATIONS - THE IMPORTANCE OF THROUGH-BOND DELOCALIZATION IN BIBENZYLIC SYSTEMS [J].

CAMAIONI, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9475-9483

[6] A kinetic evaluation of carbon-hydrogen, carbon-carbon, and carbon-silicon bond activation in benzylic radical cations [J].

Freccero, M ;

Pratt, A ;

Albini, A ;

Long, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :284-297

[7] DICARBONIUM IONS OF TRIARYLMETHYL TYPE - IONS FROM 0-, M- AND P- XYLYLENE GLYCOLS [J].

HART, H ;

SULZBERG, T ;

RAFOS, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (12) :1800-+

[8] SYNTHESIS OF DICATION SPECIES STABILIZED BY AZULENE RINGS [J].

ITO, S ;

MORITA, N ;

ASAO, T .

TETRAHEDRON LETTERS, 1992, 33 (26) :3773-3774

[9] Electron transfer initiated cyclizations:: Cyclic acetal synthesis through carbon-carbon σ-bond activation [J].

Kumar, VS ;

Floreancig, PE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) :3842-3843

[10] KINETICS OF THE REACTIONS OF CARBOXONIUM IONS AND ALDEHYDE BORON TRIHALIDE COMPLEXES WITH ALKENES AND ALLYLSILANES [J].

MAYR, H ;

GORATH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (30) :7862-7868

← 1 2 3 4 5 →