Baeyer-Villiger oxidations in ionic liquids. A facile conversion of ketones to esters and lactones

被引:33
作者
Yadav, JS [1 ]
Reddy, BVS [1 ]
Basak, AK [1 ]
Narsaiah, AV [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1246/cl.2004.248
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A variety of cyclic and acyclic ketones underwent readily oxidation with m-chloroperbenzoic acid (m-CPBA) in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4 to afford esters/lactones with high selectivity, ease of product separation and in excellent chemical yields. The reaction proceeded smoothly in ionic liquid without the need of any additional acid or base catalyst. The ketones show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly.
引用
收藏
页码:248 / 249
页数:2
相关论文
共 30 条
[1]  
Baeyer A., 1899, Ber. Dtsch. Chem. Ges., V32, P3625, DOI 10.1002/cber.189903203151
[2]   On the regioselectivity of the Baeyer-Villiger reaction of 2,6-dialkyl cyclohexanones: Application to the synthesis of sordidin, a male pheromone emitted by Cosmopolites sordidus [J].
Beauhaire, J ;
Ducrot, PH .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (03) :413-418
[3]  
CANANKOCH SS, 1989, SYNTHETIC COMMUN, V19, P829
[4]   CONSTRUCTION OF HYDROXYLATED ALKALOIDS (+/-)-MANNONOLACTAM, (+/-)-DEOXYMANNOJIRIMYCIN, AND (+/-)-PROSOPININE THROUGH AZA-ANNULATION [J].
COOK, GR ;
BEHOLZ, LG ;
STILLE, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3575-3584
[5]   New developments in catalysis using ionic liquids [J].
Gordon, CM .
APPLIED CATALYSIS A-GENERAL, 2001, 222 (1-2) :101-117
[6]  
Gottlich R, 1997, SYNLETT, P971
[7]   Total synthesis of a monocyclofarnesane dinorsesquiterpenoid isolated from mushroom ingested by beetle: Selectivity in solid-state Baeyer-Villiger reaction [J].
Hagiwara, H ;
Nagatomo, H ;
Yoshii, F ;
Hoshi, T ;
Suzuki, T ;
Ando, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2645-2648
[8]   Heterogeneous Baeyer-Villiger oxidation of ketones using m-chloroperbenzoic acid catalyzed by hydrotalcites [J].
Kaneda, K ;
Yamashita, T .
TETRAHEDRON LETTERS, 1996, 37 (26) :4555-4558
[9]  
Kotsuki H, 1999, SYNLETT, P462
[10]  
Krow G.R., 1993, ORGANIC REACTIONS, V43, P251, DOI DOI 10.1002/0471264180.OR043.03