Tris(trimethylsilyl)silane promoted radical reaction and electron-transfer reaction in benzotrifluoride

被引：26

作者：

Hasegawa, Eietsu ^{[1
]}

Ogawa, Yuki ^{[1
]}

Kakinuma, Koji ^{[1
]}

Tsuchida, Hiroyuki ^{[1
]}

Tosaka, Emi ^{[1
]}

Takizawa, Shinya ^{[1
]}

Muraoka, Hiroyasu ^{[1
]}

Saikawa, Tomoko ^{[1
]}

机构：

[1] Niigata Univ, Fac Sci, Dept Chem, Niigata 9502181, Japan

来源：

TETRAHEDRON | 2008年 / 64卷 / 33期

关键词：

D O I：

10.1016/j.tet.2008.06.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tris(trimethylsilyl)silane (TTMSS) promoted free radical reaction in benzotrifluoride (BTF) was investigated. Compared to same reaction using environmentally less desirable tri-n-butyltin hydride (TBTH) in benzene, less quantity of BTF than that of benzene can be used because of slower hydrogen atom transfer from TTMSS than that from TBTH toward primary alkyl radicals. Also, electron-transfer reactions promoted by tris(p-bromophenyl)aminium hexachloroantimonate (TBPA) and FeCl3 were conducted in BTF. Then, TBPA was found to be effective in BTF comparably to that in methylene chloride. In addition, an interesting observation that FeCl3 promoted reaction was accelerated by the addition of imidazolium salt was made. All the results suggest that BTF is a tolerable solvent for free radical reaction with TTMSS and electron-transfer reactions using TBPA as well as FeCl3. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：7724 / 7728

页数：5

共 67 条

[1] Balzani V, 2001, ELECT TRANSFER CHEM, VI-V
[2] Bauld N.L., 1992, Adv. Electron Transfer Chem, V2, P1
[3] CATION RADICAL PERICYCLIC-REACTIONS
BAULD, NL
BELLVILLE, DJ
HARIRCHIAN, B
LORENZ, KT
PABON, RA
REYNOLDS, DW
WIRTH, DD
CHIOU, HS
MARSH, BK
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (10) : 371 - 378
[4] A two step, non-stereospecific cation radical Diels-Alder reaction
Bauld, NL
Yang, JK
[J]. TETRAHEDRON LETTERS, 1999, 40 (49) : 8519 - 8522
[5] An unprecedented cation radical chain Diels-Alder polymerization leading to novel carbazole polymers
Bauld, NL
Roh, Y
[J]. TETRAHEDRON LETTERS, 2001, 42 (08) : 1437 - 1439
[6] REARRANGEMENT OF SUITABLY CONSTITUTED ARYL, ALKYL, OR VINYL RADICALS BY ACYL OR CYANO GROUP MIGRATION
BECKWITH, ALJ
OSHEA, DM
WESTWOOD, SW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) : 2565 - 2575
[7] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY
BECKWITH, ALJ
SCHIESSER, CH
[J]. TETRAHEDRON, 1985, 41 (19) : 3925 - 3941
[8] CATION-RADICALS - TRIS-(PARA-BROMOPHENYL)AMMINIUM PERCHLORATE AND HEXACHLOROANTIMONATE
BELL, FA
LEDWITH, A
SHERRINGTON, DC
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (19): : 2719 - +
[9] THE CATION-RADICAL CATALYZED DIELS-ALDER REACTION
BELLVILLE, DJ
WIRTH, DD
BAULD, NL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) : 718 - 720
[10] Berger D J., 1997, CHEM DOUBLE BONDED F, P1281, DOI DOI 10.1002/0470857234.CH22

← 1 2 3 4 5 6 7 →