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

[31] FREE-RADICAL CLOCKS
GRILLER, D
INGOLD, KU
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (09) : 317 - 323
[32] ORGANIC THERMAL-REACTIONS .63. CYCLOREVERSION REACTION OF CAGE COMPOUNDS INITIATED BY AMINIUM CATION RADICAL SALTS
HASEGAWA, E
MUKAI, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (11) : 3391 - 3392
[33] Cyclization and ring-expansion reactions involving reductive formation and oxidative ring-opening of cyclopropanol derivatives
Hasegawa, E
Tsuchida, H
Tamura, M
[J]. CHEMISTRY LETTERS, 2005, 34 (12) : 1688 - 1689
[34] Changeable reactivity of ketyl radicals derived from 2-bromomethyl-2-(3-butenyl)benzocyclic-1-alkanones depending on electron transfer conditions employed
Hasegawa, E
Takizawa, S
Iwaya, K
Kurokawa, M
Chiba, N
Yamamichi, K
[J]. CHEMICAL COMMUNICATIONS, 2002, (17) : 1966 - 1967
[35] ELECTRON-TRANSFER-INDUCED REARRANGEMENTS OF PHENYLATED TRICYCLO[4.2.0.0/2,5]OCTANE AND 1,5-CYCLOOCTADIENE
HASEGAWA, E
MUKAI, T
YANAGI, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) : 2053 - 2058
[36] First example of samarium diiodide-promoted sequential cyclization and ring-expansion reactions of α-bromomethyl cyclic β-keto esters to homologated γ-keto esters
Hasegawa, E
Kitazume, T
Suzuki, K
Tosaka, E
[J]. TETRAHEDRON LETTERS, 1998, 39 (23) : 4059 - 4062
[37] Hasegawa E., 2003, J. Photosci., V10, P61
[38] Electron transfer promoted regioselective ring-opening reaction of cyclopropyl silyl ethers
Hasegawa, Eietsu
Yamaguchi, Naoto
Muraoka, Hiroyasu
Tsuchida, Hiroyuki
[J]. ORGANIC LETTERS, 2007, 9 (15) : 2811 - 2814
[39] Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds
Hasegawa, Eietsu
Takizawa, Shinya
Seida, Takayuki
Yamaguchi, Akira
Yamaguchi, Naoto
Chiba, Naoki
Takahashi, Tomoya
Ikeda, Hiroshi
Akiyama, Kimio
[J]. TETRAHEDRON, 2006, 62 (27) : 6581 - 6588
[40] CONVENIENT SYNTHESES OF 2-NITROPHENYLSULFEN-(NPS)-IMINES BY OXIDATION OF NPS-PROTECTED AMINES AND AMINO-ACID DERIVATIVES
HEYER, J
DAPPERHELD, S
STECKHAN, E
[J]. CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (09): : 1617 - 1623

← 1 2 3 4 5 6 7 →