The Baeyer-Villiger oxidation of ketones with Oxone® in the presence of ionic liquids as solvents

被引:36
作者
Chrobok, Anna [1 ]
机构
[1] Silesian Tech Univ, Dept Chem Organ Technol & Petrochem, PL-44100 Gliwice, Poland
关键词
Baeyer-Villiger oxidation; Ionic liquids; Oxone (R); Lactones; Esters; EFFICIENT; CATALYST; TEMPERATURES; MILD;
D O I
10.1016/j.tet.2010.05.091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic and linear ketones were readily oxidised with Oxone (R) at 40 degrees C in ionic liquids as solvents and short times (2.5-20 h), affording their corresponding lactones and esters in high yields (65-95%). Both, aprotic and protic ionic liquids were used. The best conversion of ketones and the highest yields of products were obtained with 1-buty-3-methylimidazolium tetrafluoroborate and 1-methylimidazolium acetate as solvents. These ionic liquids were also efficiently recycled in the Baeyer Villiger reaction without significant loss of activity. Several factors, such as the partial solubility of KHSO5 in the ionic liquid, its viscosity and the presence of a proton in protic ionic liquids, have an influence on the course of the reaction. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6212 / 6216
页数:5
相关论文
共 31 条
[1]  
[Anonymous], SPECTR DAT ORG COMP
[2]  
Baeyer A., 1899, BER DTSCH CHEM GES, V32, P3625, DOI DOI 10.1002/CBER.189903203151
[3]  
BAJ S, 2008, SYNTHETIC COMMUN, V38, P1
[4]   The Baeyer-Villiger oxidation of ketones with bis(trimethylsilyl) peroxide in the presence of ionic liquids as the solvent and catalyst [J].
Baj, Stefan ;
Chrobok, Anna ;
Slupska, Roksana .
GREEN CHEMISTRY, 2009, 11 (02) :279-282
[5]   Hydrophobic, highly conductive ambient-temperature molten salts [J].
Bonhote, P ;
Dias, AP ;
Papageorgiou, N ;
Kalyanasundaram, K ;
Gratzel, M .
INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178
[6]  
Brink G.J. T., 2004, Chem. Rev, V104, P4105, DOI DOI 10.1021/CR030011L
[7]   Supported hydrogensulfate ionic liquid catalysis in Baeyer-Villiger reaction [J].
Chrobok, Anna ;
Baj, Stefan ;
Pudlo, Wojciech ;
Jarzebski, Andrzej .
APPLIED CATALYSIS A-GENERAL, 2009, 366 (01) :22-28
[8]   Phase transition and decomposition temperatures, heat capacities and viscosities of pyridinium ionic liquids [J].
Crosthwaite, JM ;
Muldoon, MJ ;
Dixon, JK ;
Anderson, JL ;
Brennecke, JF .
JOURNAL OF CHEMICAL THERMODYNAMICS, 2005, 37 (06) :559-568
[9]   [BPy]HSO4 acidic ionic liquid as a novel, efficient, and environmentally benign catalyst for synthesis of 1,5-benzodiazepines under mild conditions [J].
Du, Yuying ;
Tian, Fuli ;
Zhao, Wenzhi .
SYNTHETIC COMMUNICATIONS, 2006, 36 (12) :1661-1669
[10]   Physical properties of pure 1-ethyl-3-methylimidazolium ethylsulfate and its binary mixtures with ethanol and water at several temperatures [J].
Gomez, Elena ;
Gonzalez, Begona ;
Calvar, Noelia ;
Tojo, Emilia ;
Dominguez, Angeles .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2006, 51 (06) :2096-2102