A Cp2TiCl2-Me3Al (1:4) reagent system:: An efficient reagent for generation of allylic titanocene derivatives from vinyl halides, vinyl ethers and carboxylic esters

被引：10

作者：

Hanzawa, Y ^{[1
]}

Kowase, N ^{[1
]}

Momose, S ^{[1
]}

Taguchi, T ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(98)00681-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reagent prepared in advance by stirring a mixture of a Cp2TiCl2-Me3Al(a 1 : 4 ratio) reagent system in toluene for 3 days is found to be effective in generating allylic titanocene on treatment with vinyl halides, vinyl ethers and carboxylic esters in THF. The process for the generation of an allylic titanocene species from these starting materials was suggested to proceed through a formation of titanacyclobutane and the subsequent elimination of the halogen or alkoxyl group. The generated allylic titanocene intermediate was proved to be an allylic TI(IV) species and showed the typical reactivity to carbonyl compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：11387 / 11398

页数：12

共 36 条

[1] CONVERSION OF MONO-ALKYL OLEFINS TO 1,1-DIALKYL OLEFINS BY REACTION WITH BIS(CYCLOPENTADIENYL)TITANIUM DICHLORIDE TRIALKYLALUMINUM
BARBER, JJ
WILLIS, C
WHITESIDES, GM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (20) : 3603 - 3604
[2] REACTIONS OF 2-METHYLENEALLYL DIANION WITH ALDEHYDES, KETONES, EPOXIDES, AND ALLYL HALIDES
BATES, RB
BEAVERS, WA
GORDON, B
MILLS, NS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) : 3800 - 3803
[3] CP2TICH2 COMPLEXES IN SYNTHETIC APPLICATIONS
BROWNWENSLEY, KA
BUCHWALD, SL
CANNIZZO, L
CLAWSON, L
HO, S
MEINHARDT, D
STILLE, JR
STRAUS, D
GRUBBS, RH
[J]. PURE AND APPLIED CHEMISTRY, 1983, 55 (11) : 1733 - 1744
[4] REACTION OF CP2TI=CH2 WITH ORGANIC HALIDES - EVIDENCE FOR A RADICAL MECHANISM
BUCHWALD, SL
ANSLYN, EV
GRUBBS, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) : 1766 - 1768
[5] CARDIN DJ, 1986, CHEM ORGANOZIRCONIUM
[6] CHINO M, 1994, SYNLETT, P359
[7] NON-WITTIG TYPE REACTION OF TEBBE REAGENT WITH ACYL CHLORIDE
CHOU, TS
HUANG, SB
[J]. TETRAHEDRON LETTERS, 1983, 24 (21) : 2169 - 2170
[8] DRAGUTON V, 1985, OLEFIN METATHESIS RI
[9] Grubbs R.H., 1982, COMPREHENSIVE ORGANO, V8, P499
[10] Generation of allylic titanocene derivatives from vinyl halides and a Cp2TiCl2-Me3Al reagent system
Hanzawa, Y
Kowase, N
Taguchi, T
[J]. TETRAHEDRON LETTERS, 1998, 39 (07) : 583 - 586

← 1 2 3 4 →