Cation and leaving group effects in isosorbide alkylation under microwave in phase transfer catalysis

被引：33

作者：

Chatti, S ^{[1
]}

Bortolussi, M ^{[1
]}

Loupy, A ^{[1
]}

机构：

[1] Univ Paris 11, ICMO, Lab React Select Supports, UMR 8615, F-91405 Orsay, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 20期

关键词：

cation and leaving group; alkylation; phase transfer catalysis; microwave;

D O I：

10.1016/S0040-4020(01)00318-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have studied cation, salt, leaving group effects and influence of catalyst under phase transfer catalysis conditions using concomitant microwave irradiation during di-n-octylation of isosorbide. A small amount of solvent was necessary to control temperature and to provide good yields within a few minutes. The yields were dramatically improved when compared to conventional heating under the same conditions, in spite of similar profiles of raising in temperature. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4365 / 4370

页数：6

共 37 条

[1] Synthesis of a novel starch-derived AB-type polyurethane [J].

Bachmann, F ;

Reimer, J ;

Ruppenstein, M ;

Thiem, J .

MACROMOLECULAR RAPID COMMUNICATIONS, 1998, 19 (01) :21-26

[2]

Bogdal D, 1996, SYNLETT, P873

[3] AN EASY ROUTE TO SYNTHESIZE 1,5-ARYLODIAZEPIN-2-ONES [J].

BOUGRIN, K ;

BENNANI, AK ;

TETOUANI, SF ;

SOUFIAOUI, M .

TETRAHEDRON LETTERS, 1994, 35 (45) :8373-8376

[4] AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS [J].

BUNNETT, JF ;

ZAHLER, RE .

CHEMICAL REVIEWS, 1951, 49 (02) :273-412

[5] Scope and utility of a new soluble copper catalyst [CuBr-LiSPh-LiBr-THF]: A comparison with other copper catalysts in their ability to couple one equivalent of a grignard reagent with an alkyl sulfonate [J].

Burns, DH ;

Miller, JD ;

Chan, HK ;

Delaney, MO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2125-2133

[6] SPECIFIC CATION PARTICIPATION IN ALKALI-CARBANION INITIATED EPOXIDE CLEAVAGE REACTIONS [J].

CHANG, CJ ;

KIESEL, RF ;

HOGENESC.TE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (25) :8446-8448

[7] Synthesis of diethers derived from dianhydrohexitols by phase transfer catalysis under microwave [J].

Chatti, S ;

Bortolussi, M ;

Loupy, A .

TETRAHEDRON LETTERS, 2000, 41 (18) :3367-3370

[8] Synthesis of new diols derived from dianhydrohexitols ethers under microwave-assisted phase transfer catalysis [J].

Chatti, S ;

Bortolussi, M ;

Loupy, A .

TETRAHEDRON, 2000, 56 (32) :5877-5883

[9] NEW POLYURETHANES BASED ON DIPHENYLMETHANE DIISOCYANATE AND 1,4/3,6-DIANHYDROSORBITOL .1. MODEL KINETIC-STUDIES AND CHARACTERIZATION OF THE HARD SEGMENT [J].

COGNETGEORJON, E ;

MECHIN, F ;

PASCAULT, JP .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 1995, 196 (11) :3733-3751

[10] Direct evidence for the hydroxide extraction mechanism in the phase transfer catalyzed cyclopropanation of 4-halobutyronitrile in a solid-liquid system [J].

Cohen, S ;

Zoran, A ;

Sasson, Y .

TETRAHEDRON LETTERS, 1998, 39 (52) :9815-9818

← 1 2 3 4 →