Oxidation of beta,gamma-unsaturated ketones with molecular oxygen catalyzed by metal phthalocyanines and porphyrins: A practical synthesis of oxophorone

被引:0
作者
Ito, N
Etoh, T
Hagiwara, H
Kato, M
机构
[1] NIIGATA UNIV,GRAD SCH SCI & TECHNOL,NIIGATA 95021,JAPAN
[2] TOHOKU UNIV,INST CHEM REACT SCI,AOBA KU,SENDAI,MIYAGI 98077,JAPAN
来源
SYNTHESIS-STUTTGART | 1997年 / 02期
关键词
oxidation with molecular oxygen; beta; gamma-unsaturated ketones; transition metal phthalocyanine; transition metal porphyrin; oxophorone;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidation of 3,5,5-trimethylcyclohex-3-en-1-one (1) with molecular oxygen catalyzed by metal phthalocyanines (Pc) and 5,10,15,20-tetraphenylporphyrins (TPP) including Mn(II), Mn(III), Fe(II), Fe(III), Co(II), Cu(II), and Ru(II) to 3,5,5-trimethylcyclohex-2-ene-1,4-dione (2) was studied. TPPMn(III)Cl showed an excellent catalytic activity, affording 2 in 93% yield and 12500 turnover number.
引用
收藏
页码:153 / &
页数:4
相关论文
共 30 条
[1]  
[Anonymous], 1971, CAROTENOIDS
[2]  
BAIN Z, 1984, J CHEM ECOL, V10, P451
[3]  
BECKER JJ, 1975, Patent No. 2457157
[4]   SELECTIVE OXIDATION OF 3,5,5-TRIMETHYLCYCLOHEXENE-3 ONE (BETA-ISOPHORONE) TO 3,5,5-TRIMETHYLCYCLOHEXENE-1,4 DIONE BY OXYGEN CATALYZED BY MNII OR COII CHELATES [J].
COSTANTINI, M ;
DROMARD, A ;
JOUFFRET, M ;
BROSSARD, B ;
VARAGNAT, J .
JOURNAL OF MOLECULAR CATALYSIS, 1980, 7 (01) :89-97
[5]  
COSTANTINI M, 1977, Patent No. 2335486
[6]  
COSTANTINI M, 1977, Patent No. 2657386
[7]   NOVEL SYNTHESIS OF 3,5,5-TRIMETHYL-4-(2-BUTENYLIDENE)-CYCLOHEX-2-EN-1-ONE, A MAJOR CONSTITUENT OF BURLEY TOBACCO FLAVOR [J].
DEMOLE, E ;
ENGGIST, P .
HELVETICA CHIMICA ACTA, 1974, 57 (07) :2087-2091
[8]   NEUTRAL AROMA CONSTITUENTS IN BURLEY TOBACCO [J].
FUJIMORI, T ;
KASUGA, R ;
MATSUSHITA, H ;
KANEKO, H ;
NOGUCHI, M .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1976, 40 (02) :303-315
[9]   OXYGENATION OF (E)-4-STILBENOLS CATALYZED BY COBALT(II) SCHIFF-BASE CHELATES [J].
GANESHPURE, PA ;
SATISH, S .
TETRAHEDRON LETTERS, 1988, 29 (50) :6629-6632
[10]   SELECTIVE QUINONE FORMATION BY AROMATIC OXIDATION WITH HETEROAROMATIC N-OXIDE CATALYZED BY RUTHENIUM PORPHYRIN [J].
HIGUCHI, T ;
SATAKE, C ;
HIROBE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (34) :8879-8880