HIGHLY EFFICIENT AND MILD SYNTHESIS OF NITRONES BY CATALYTIC-OXIDATION OF HYDROXYLAMINES WITH TETRA-N-PROPYLAMMONIUM PERRUTHENATE

被引:65
作者
GOTI, A
DESARLO, F
ROMANI, M
机构
[1] Centro di Studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, C.N.R., Dip. di Chimica Organica Ugo Schiff, I-50121 Firenze
关键词
D O I
10.1016/S0040-4039(00)78275-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidation of N,N-disubstituted hydroxylamines by N-methylmorpholine N-oxide (NMO) and catalytic amounts of tetra-n-propylammonium perruthenate (TPAP) at room temperature occurs very rapidly to give the corresponding nitrones, which can be trapped by dipolarophiles present in the reaction mixture, in excellent yields. A competitive experiment in the presence of a primary alcohol gave a >50:1 nitrone to aldehyde ratio.
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页码:6571 / 6574
页数:4
相关论文
共 20 条
[1]   SYNTHESIS OF TRANS-2,6-DIALKYLPIPERIDINES BY INTRAMOLECULAR AMIDOMERCURIATION AND BY 1,3-CYCLOADDITION OF ALKENES TO 2-METHYL-2,3,4,5-TETRAHYDROPYRIDINE OXIDE [J].
ADAMS, DR ;
CARRUTHERS, W ;
WILLIAMS, MJ ;
CROWLEY, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1507-1513
[2]   THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF 1,3-DIPOLAR CYCLO-ADDITION OF A CYCLIC NITRONE [J].
ALI, SA ;
WAZEER, MIM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :597-605
[3]   ONE-FLASK TRANSFORMATION OF SECONDARY-AMINES TO NITRONES BY OXIDATION WITH HYDROGEN-PEROXIDE MEDIATED BY TRISCETYLPYRIDINIUM TETRAKIS OXODIPEROXOTUNGSTO-PHOSPHATE (PCWP) - SOME MECHANISTIC CONSIDERATIONS [J].
BALLISTRERI, FP ;
CHIACCHIO, U ;
RESCIFINA, A ;
TOMASELLI, GA ;
TOSCANO, RM .
TETRAHEDRON, 1992, 48 (40) :8677-8684
[4]   KINETIC RESOLUTION IN 1,3-DIPOLAR CYCLOADDITION OF TARTARIC ACID-DERIVED NITRONES TO 2,3-DIHYDRO-1-PHENYL-1H-PHOSPHOLES - AN ENANTIOSELECTIVE APPROACH TO THE 2,2'-COUPLED PYRROLIDINE PHOSPHOLANE RING-SYSTEM [J].
BRANDI, A ;
CICCHI, S ;
GOTI, A ;
KOPROWSKI, M ;
PIETRUSIEWICZ, KM .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1315-1318
[5]  
BRANDI A, 1993, SYNLETT, P1
[6]  
Breuer E., 1982, CHEM AMINO NITROSO N
[7]   NEW SYNTHESIS OF 5-MEMBERED CYCLIC NITRONES FROM TARTARIC ACID [J].
CICCHI, S ;
HOLD, I ;
BRANDI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5274-5275
[8]  
DeShong P., 1988, ADV CYCLOADDITION, VI
[9]   REACTIONS AT HIGH-PRESSURES - [3+2] DIPOLAR CYCLOADDITION OF NITRONES WITH VINYL ETHERS [J].
DICKEN, CM ;
DESHONG, P .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2047-2051
[10]  
DOPP D, 1990, HOUBENWEYL METHOD EB, V14