A Mild and Highly Efficient Catalyst for Beckmann Rearrangement, BF3•OEt2

被引：19

作者：

An Na ^{[1
]}

Pi Hongjun ^{[1
]}

Liu Lifeng ^{[1
]}

Du Wenting ^{[1
,2
]}

Deng Weiping ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

[2] Zhejiang Med Coll, Dept Pharm, Hangzhou 310053, Zhejiang, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2011年 / 29卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Beckmann rearrangement; BF3 center dot OEt2; catalyst; amide; ACIDIC IONIC LIQUIDS; CYCLOHEXANONE OXIME; FACILE CONVERSION; EPSILON-CAPROLACTAM; SUPERCRITICAL WATER; BORON FLUORIDE; ACTIVE-SITES; KETOXIMES; DEHYDRATION; CHLORIDE;

D O I：

10.1002/cjoc.201190193

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

BF3 center dot OEt2 (Boron trifluoride etherate), an inexpensive and commercially easily available Lewis acid stoichiometrically employed for Beckamann rearrangement in general, was now found to efficiently catalyze Beckmann rearrangement of ketoximes into their corresponding amides (up to 99% yield) in anhydrous acetonitrile under reflux temperature.

引用

页码：947 / 950

页数：4

共 54 条

[1] Improved procedures for the Beckmann rearrangement: the reaction of ketoxime carbonates with boron trifluoride etherate [J].

Anilkumar, R ;

Chandrasekhar, S .

TETRAHEDRON LETTERS, 2000, 41 (28) :5427-5429

[2] Rhodium-catalyzed Beckmann rearrangement [J].

Arisawa, M ;

Yamaguchi, M .

ORGANIC LETTERS, 2001, 3 (02) :311-312

[3] Beckmann rearrangement of oximes catalyzed by cyanuric chloride in ionic liquids [J].

Betti, Cecilia ;

Landini, Dario ;

Maia, Angelamaria ;

Pasia, Maurizio .

SYNLETT, 2008, (06) :908-910

[4] Hydrogen bond driven chemical reactions:: Beckmann rearrangement of cyclohexanone oxime into ε-caprolactam in supercritical water [J].

Boero, M ;

Ikeshoji, T ;

Liew, CC ;

Terakura, K ;

Parrinello, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (20) :6280-6286

[5] Influences of ethylenediamine treatment of Silicalite-1 on the catalytic vapor-phase Beckmann rearrangement of cyclohexanone oxime [J].

Bu, Yifeng ;

Wang, Yaquan ;

Zhang, Yongjie ;

Wang, Li ;

Mi, Zhentao ;

Wu, Wei ;

Min, Enze ;

Fu, Songbao .

CATALYSIS COMMUNICATIONS, 2007, 8 (01) :16-20

[6] ε-caprolactam:: New by-product free synthesis routes [J].

Dahlhoff, G ;

Niederer, JPM ;

Hoelderich, WF .

CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2001, 43 (04) :381-441

[7] RuCl3 catalyzed facile conversion of arylalkyl ketoximes to amides [J].

De, SK .

SYNTHETIC COMMUNICATIONS, 2004, 34 (18) :3431-3434

[8] Facile Beckmann rearrangement of ketoximes mediated by yttrium triflate [J].

De, SK .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2004, 36 (04) :383-386

[9]

De SK, 2004, J CHEM RES, P131

[10] Beckmann-rearrangement of cyclododecanone oxime to ω-laurolactam in the gas phase [J].

Eickelberg, W. ;

Hoelderich, W. F. .

JOURNAL OF CATALYSIS, 2009, 263 (01) :42-55

← 1 2 3 4 5 6 →