BECKMANN REARRANGEMENT OF OXIMES CATALYZED WITH TETRABUTYLAMMONIUM PERRHENATE AND TRIFLUOROMETHANESULFONIC ACID

被引:35
作者
KUSAMA, H [1 ]
YAMASHITA, Y [1 ]
NARASAKA, K [1 ]
机构
[1] UNIV TOKYO, GRAD SCH SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN
关键词
D O I
10.1246/bcsj.68.373
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Beckmann rearrangement of oximes is catalyzed by a combined use of tetrabutylammonium perrhenate (Bu(4)NReO(4) and trifluoromethanesulfonic acid in nitromethane under azeotropic conditions, giving amides in high yield. By employing this catalytic system, amides can be prepared directly from ketones and hydroxylamine hydrochloride.
引用
收藏
页码:373 / 377
页数:5
相关论文
共 13 条
[1]   SYNTHETIC ASPECTS OF AN ASYMMETRIC NITROGEN-INSERTION PROCESS - PREPARATION OF CHIRAL, NON-RACEMIC CAPROLACTAMS AND VALEROLACTAMS - TOTAL SYNTHESIS OF (-)-ALLOYOHIMBANE [J].
AUBE, J ;
WANG, YG ;
HAMMOND, M ;
TANOL, M ;
TAKUSAGAWA, F ;
VANDERVELDE, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4879-4891
[2]   REAGENTS AND SYNTHETIC METHODS 33 IMPROVED ONE-STEP BECKMANN REARRANGEMENT FROM KETONES AND HYDROXYLAMINE IN FORMIC-ACID SOLUTION [J].
GANBOA, I ;
PALOMO, C .
SYNTHETIC COMMUNICATIONS, 1983, 13 (11) :941-944
[3]  
Gawley R.E, 2004, ORG REACT, DOI 10.1002/0471264180.or035.01
[4]  
Gutmann V., 1978, DONOR ACCEPTOR APPRO
[5]  
HARADA T, 1991, SYNTHESIS-STUTTGART, P1216
[6]   VAPOR-PHASE BECKMANN REARRANGEMENT OF CYCLOHEXANONE OXIME OVER BORIA-HYDROXYAPATITE CATALYST [J].
IZUMI, Y ;
SATO, S ;
URABE, K .
CHEMISTRY LETTERS, 1983, (10) :1649-1652
[7]   CATALYTIC BECKMANN REARRANGEMENT OF OXIMES IN HOMOGENEOUS LIQUID-PHASE [J].
IZUMI, Y .
CHEMISTRY LETTERS, 1990, (12) :2171-2174
[8]   THE CATALYTIC BECKMANN REARRANGEMENT OF KETOXIME TRIMETHYLSILYL ETHERS USING AN ANTIMONY(V) SALT [J].
MUKAIYAMA, T ;
HARADA, T .
CHEMISTRY LETTERS, 1991, (09) :1653-1656
[9]   REARRANGEMENT OF ALLYLIC AND PROPARGYLIC ALCOHOLS CATALYZED BY THE COMBINED USE OF TETRABUTYLAMMONIUM PERRHENATE(VII) AND PARA-TOLUENESULFONIC ACID [J].
NARASAKA, K ;
KUSAMA, H ;
HAYASHI, Y .
TETRAHEDRON, 1992, 48 (11) :2059-2068
[10]   BECKMANN REARRANGEMENT CATALYZED BY THE COMBINED USE OF TETRABUTYLAMMONIUM PERRHENATE(VII) AND TRIFLUOROMETHANESULFONIC ACID [J].
NARASAKA, K ;
KUSAMA, H ;
YAMASHITA, Y ;
SATO, H .
CHEMISTRY LETTERS, 1993, (03) :489-492