Oxidative cleavage of vic-diols to aldehydes with dioxygen catalyzed by Ru(PPh3)3Cl2 on active carbon

被引:71
作者
Takezawa, E [1 ]
Sakaguchi, S [1 ]
Ishii, Y [1 ]
机构
[1] Kansai Univ, Fac Engn & High Technol, Dept Appl Chem, Res Ctr, Suita, Osaka 5648680, Japan
关键词
D O I
10.1021/ol990117w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A variety of vic-diols were first successfully cleaved to the corresponding aldehydes with dioxygen catalyzed by RU(PPh3)(3)Cl-2 on active carbon in fair to good yields. For example, treatment of 1,2-octandiol and 1,2-cyclooctanediol with dioxygen in the presence of Ru(PPh3)(3)Cl-2/C in PhCF3 at 60 degrees C for 15 h produced heptanal and 1,8-octanedial in 77% and 76% yields, respectively.
引用
收藏
页码:713 / 715
页数:3
相关论文
共 18 条
[1]   CATALYTIC OXIDATIVE CLEAVAGE OF VICINAL DIOLS AND RELATED OXIDATIONS BY RUTHENIUM PYROCHLORE OXIDES - NEW CATALYSTS FOR LOW-TEMPERATURE OXIDATIONS WITH MOLECULAR-OXYGEN [J].
FELTHOUSE, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7566-7568
[2]   An efficient aerobic oxidation of various organic compounds catalyzed by mixed addenda heteropolyoxometalates containing molybdenum and vanadium [J].
Fujibayashi, S ;
Nakayama, K ;
Hamamoto, M ;
Sakaguchi, S ;
Nishiyama, Y ;
Ishii, Y .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 110 (02) :105-117
[3]   Selective aerobic oxidation of primary alcohols catalyzed by a Ru(PPh3)3Cl2/hydroquinone system [J].
Hanyu, A ;
Takezawa, E ;
Sakaguchi, S ;
Ishii, Y .
TETRAHEDRON LETTERS, 1998, 39 (31) :5557-5560
[4]  
Hudlicky M., 1981, OXIDATIONS ORGANIC C, P159
[5]   HYDROGEN-PEROXIDE OXIDATION CATALYZED BY HETEROPOLY ACIDS COMBINED WITH CETYLPYRIDINIUM CHLORIDE - EPOXIDATION OF OLEFINS AND ALLYLIC ALCOHOLS, KETONIZATION OF ALCOHOLS AND DIOLS, AND OXIDATIVE CLEAVAGE OF 1,2-DIOLS AND OLEFINS [J].
ISHII, Y ;
YAMAWAKI, K ;
URA, T ;
YAMADA, H ;
YOSHIDA, T ;
OGAWA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3587-3593
[6]  
IWAHAMA T, 1995, TETRAHEDRON LETT, V36, P6293
[7]  
KANADA K, 1988, CHEM LETT, P1295
[8]   Tetra-n-propylammonium perruthenate (TPAP)-catalysed oxidations of alcohols using molecular oxygen as a co-oxidant [J].
Lenz, R ;
Ley, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (22) :3291-3292
[9]  
MARCO IE, 1997, J AM CHEM SOC, V119, P12661
[10]   BIOMIMETIC OXIDATION WITH MOLECULAR-OXYGEN - SELECTIVE CARBON CARBON BOND-CLEAVAGE OF 1,2-DIOLS BY MOLECULAR-OXYGEN AND DIHYDROPYRIDINE IN THE PRESENCE OF IRON PORPHYRIN CATALYSTS [J].
OKAMOTO, T ;
SASAKI, K ;
OKA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1187-1196