Photochemical nucleophile - Olefin combination, aromatic substitution reaction. Its synthetic development and mechanistic exploration

被引：76

作者：

Mangion, D ^{[1
]}

Arnold, DR ^{[1
]}

机构：

[1] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4J3, Canada

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2002年 / 35卷 / 05期

关键词：

D O I：

10.1021/ar010108z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The photochemical nucleophile-olefin combination,: aromatic substitution (photo-NOCAS) reaction has been a cornerstone of research in our laboratory for several years.,In this Account we present'an overview of the mechanistic exploration and rational- ization of this photoinduced electron transfer reaction. We have investigated the mechanism and defined the synthetic scope and limitations by variations in reaction conditions and structural modification of the substrates. During Our studies, We have come across several other pathways in competition with the photo NOCAS reaction that dominate once specific conditions are altered. These alternative reactions are also discussed briefly.

引用

页码：297 / 304

页数：8

共 50 条

[1] RADICAL IONS IN PHOTOCHEMISTRY .3. PHOTOSENSITIZED (ELECTRON-TRANSFER) CLEAVAGE OF BETA-PHENETHYL ETHERS [J].

ARNOLD, DR ;

MAROULIS, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (19) :5931-5936

[2] Photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction .13. The scope and limitations of the reaction with cyanide anion as the nucleophile [J].

Arnold, DR ;

McManus, KA ;

Chan, MSW .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (08) :1055-1075

[3] RADICAL IONS IN PHOTOCHEMISTRY .32. PHOTOCHEMICAL NUCLEOPHILE OLEFIN COMBINATION, AROMATIC-SUBSTITUTION (PHOTO-NOCAS) REACTION .6. METHANOL, NONCONJUGATED DIENES, AND 1,4-DICYANOBENZENE [J].

ARNOLD, DR ;

MCMANUS, KA ;

DU, XY .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (02) :415-429

[4] PHOTOSENSITIZED (ELECTRON-TRANSFER) [2E+4E] DIMERIZATION AND CROSS-CYCLOADDITION OF PHENYLATED OLEFINS - TRAPPING THE INTERMEDIATE [J].

ARNOLD, DR ;

BORG, RM ;

ALBINI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) :138-139

[5] THE EFFECT OF META-CYANO OR PARA-CYANO SUBSTITUTION ON THE REACTIVITY OF THE RADICAL CATIONS OF ARYLALKENES AND ALKANES - RADICAL IONS IN PHOTOCHEMISTRY .34. [J].

ARNOLD, DR ;

DU, XY ;

CHEN, J .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (03) :307-318

[6] RADICAL IONS IN PHOTOCHEMISTRY .12. THE PHOTOADDITION OF OLEFINS TO CYANO AROMATIC-COMPOUNDS IN POLAR-SOLVENTS [J].

ARNOLD, DR ;

WONG, PC ;

MAROULIS, AJ ;

CAMERON, TS .

PURE AND APPLIED CHEMISTRY, 1980, 52 (12) :2609-2619

[7] RADICAL IONS IN PHOTOCHEMISTRY .18. THE PHOTOSENSITIZED (ELECTRON-TRANSFER) TAUTOMERIZATION OF ALKENES - THE 1,1-DIPHENYL ALKENE SYSTEM [J].

ARNOLD, DR ;

MINES, SA .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09) :2312-2314

[8] RADICAL IONS IN PHOTOCHEMISTRY .20. THE PHOTOCHEMICAL NUCLEOPHILE-OLEFIN COMBINATION, AROMATIC-SUBSTITUTION REACTION .2. METHANOL - CYCLIC OLEFINS, 1,4-DICYANOBENZENE [J].

ARNOLD, DR ;

SNOW, MS .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (12) :3012-3026

[9] Photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction .12. Factors controlling the regiochemistry of the reaction with alcohol as the nucleophile [J].

Arnold, DR ;

Chan, MSW ;

McManus, KA .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (11) :2143-2166

[10] THE PHOTOCHEMICAL NUCLEOPHILE OLEFIN COMBINATION, AROMATIC-SUBSTITUTION (PHOTO-NOCAS) REACTION .5. METHANOL-MONOTERPENES (ALPHA-PINENE AND BETA-PINENE, TRICYCLENE, AND NOPOL), 1,4-DICYANOBENZENE [J].

ARNOLD, DR ;

DU, XY .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (02) :403-414

← 1 2 3 4 5 →