OXIDATION OF VIC-DIOLS TO ALPHA-DICARBONYL COMPOUNDS USING THE OXOAMMONIUM SALT DERIVED FROM 4-ACETAMIDO-TEMPO AND P-TOLUENESULFONIC ACID

被引:61
作者
BANWELL, MG
BRIDGES, VS
DUPUCHE, JR
RICHARDS, SL
WALTER, JM
机构
[1] School of Chemistry, University of Melbourne, Victoria 3052, Parkville
关键词
D O I
10.1021/jo00100a040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both open-chain and cyclic vicinal-diols are oxidized to the corresponding alpha-dicarbonyl compound by the oxoammonium salt derived from 4-acetamido-TEMPO and p-toluenesulfonic acid. With certain exceptions, yields are as high or higher than those obtained when Swern reagents are used to effect the same conversions.
引用
收藏
页码:6338 / 6343
页数:6
相关论文
共 18 条
[1]   OXIDATION OF VICINAL DIOLS TO ALPHA-DICARBONYL COMPOUNDS BY TRIFLUOROACETIC-ANHYDRIDE ACTIVATED DIMETHYLSULFOXIDE [J].
AMON, CM ;
BANWELL, MG ;
GRAVATT, GL .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4851-4855
[2]   OXIDATION OF DIOLS WITH ALKALI HYPOCHLORITES CATALYZED BY OXAMMONIUM SALTS UNDER 2-PHASE CONDITIONS [J].
ANELLI, PL ;
BANFI, S ;
MONTANARI, F ;
QUICI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2970-2972
[3]  
Banwell M. G., 1991, ADV STRAIN ORGANIC C, V1, P19
[4]   STUDIES IN THE TRICYCLOOCTANE SERIES .I. DEHYDROHALOGENATION OF SOME BIS-HALOGENOCARBENE ADDUCTS OF CYCLOHEXADIENES [J].
BANWELL, MG ;
HALTON, B .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (04) :849-858
[5]   CIS-DIHYDROCATECHOLS AS PRECURSORS TO HIGHLY OXYGENATED TROPONOIDS - A FULLY REGIOCONTROLLED SYNTHESIS OF 3,4-DIMETHOXY-ALPHA-TROPOLONE [J].
BANWELL, MG ;
CORBETT, M ;
MACKAY, MF ;
RICHARDS, SL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11) :1329-1334
[6]   NEW METHODS FOR THE SYNTHESIS OF TROPONOID COMPOUNDS [J].
BANWELL, MG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (01) :1-36
[8]   A FULLY REGIOCONTROLLED SYNTHESIS OF DESACETAMIDOISOCOLCHICINE - FORMAL TOTAL SYNTHESIS OF COLCHICINE [J].
BANWELL, MG ;
LAMBERT, JN ;
GULBIS, JM ;
MACKAY, MF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (20) :1450-1452
[9]   A VERSATILE NEW STRATEGY FOR THE SYNTHESIS OF TROPOLONES [J].
BANWELL, MG ;
ONRUST, R .
TETRAHEDRON LETTERS, 1985, 26 (37) :4543-4546
[10]   MANY-MEMBERED CARBON RINGS .7. CYCLOOCTYNE [J].
BLOMQUIST, AT ;
LIU, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (09) :2153-2154