GENERATION AND REACTIONS OF TRIFLUOROACETIMIDOYL RADICALS

被引：44

作者：

DANOH, Y ^{[1
]}

MATTA, H ^{[1
]}

UEMURA, J ^{[1
]}

WATANABE, H ^{[1
]}

UNEYAMA, K ^{[1
]}

机构：

[1] OKAYAMA UNIV, FAC ENGN, DEPT APPL CHEM, OKAYAMA 700, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 05期

关键词：

D O I：

10.1246/bcsj.68.1497

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Aryltrifluoroacetimidoyl radicals have been generated by three different methods: the tin-radical promoted deiodination and photochemical homolysis of imidoyl iodides and the thermal homolysis of imidoyl azo-compounds. N-[2-(1-alkynyl)phenyl]trifluoroacetimidoyl iodides have been converted to trifluoromethylated indoles by the tin-radical promoted homolysis of the carbon-iodine bond followed by intramolecular cyclization. The photolysis of trifluoroacetimidoyl iodides enabled both intra- and intermolecular cyclization to indoles and quinolines. Likewise, thermal reactions of N-(2,2,2-trifluoro-1-tritylazoethylidene) anilines provided trifluoromethylated quinolines and indoles.

引用

页码：1497 / 1507

页数：11

共 48 条

[1] PHOTOLYSIS OF HALOGENS IN PRESENCE OF TRIFLUOROACETALDEHYDE - SOME REACTIONS OF TRIFLUOROACETYL RADICAL [J].

AMPHLETT, JC ;

WHITTLE, E .

TRANSACTIONS OF THE FARADAY SOCIETY, 1967, 63 (529P) :80-&

[2] INTRAMOLECULAR ADDITION OF CARBON-CENTERED TINTHIOIMIDOYL RADICALS TO CARBON CARBON DOUBLE-BONDS - SYNTHESIS OF GAMMA-THIOLACTAMS AND DELTA-THIOLACTAMS [J].

BACHI, MD ;

DENENMARK, D .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3442-3444

[3] CYCLIZATIONS OF ENE RADICALS - IMIDOYL RADICALS AS INTERMEDIATES IN THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS [J].

BACHI, MD ;

DENENMARK, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1886-1888

[4] FORMATION OF TETRAHYDROINDANES AND RELATED SYSTEMS BY METHODS INVOLVING RADICAL RING-CLOSURE [J].

BECKWITH, ALJ ;

OSHEA, DM ;

ROBERTS, DH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (23) :1445-1446

[5] SYNTHESIS AND SOLVOLYSIS OF (Z)/(E)-1-METHYL-2-[2-(1-PROPYN-1-YL)PHENYL]VINYL TRIFLATE AND 1-METHYLENE-2-[2-(1-PROPYN-1-YL)PHENYL]ETHYL TRIFLATE [J].

BLECKMANN, W ;

HANACK, M .

CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (10) :3021-3033

[6]

CHANDY MJ, 1975, TETRAHEDRON LETT, P4515

[7]

CLEMENCE F, Patent No. 12639

[8] 4+1 RADICAL ANNULATIONS WITH ISONITRILES - A SIMPLE ROUTE TO CYCLOPENTA-FUSED QUINOLINES [J].

CURRAN, DP ;

LIU, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2127-2132

[9] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (06) :417-439

[10] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (07) :489-513

← 1 2 3 4 5 →