NATURAL ABUNDANCE O-17 NMR SPECTROSCOPIC STUDY OF QUINONE METHIDES

被引:3
作者
BOYKIN, DW [1 ]
KUMAR, A [1 ]
SHEVCHENKO, SM [1 ]
机构
[1] LENINGRAD FOREST TECH ACAD,DEPT ORGAN CHEM,LENINGRAD 194018,USSR
关键词
NATURAL ABUNDANCE O-17 NMR; QUINONE METHIDES; 10-METHYLENEANTHRONES;
D O I
10.1002/mrc.1260300105
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The O-17 NMR chemical shift data for a series of substituted 10-methyleneanthrones and related 10-alkylanthrones in acetonitrile solution at 75-degrees-C are reported. The O-17 NMR chemical shift value of 10-methyleanthrone is shielded by ca. 35 ppm compared with that of anthraquinone. The chemical shifts of the 10-methyleneanthrones range from 493 ppm for 10-bromomethyleneanthrone to 440 ppm for 10-diethylaminomethyleneanthrone. A correlation of the O-17 NMR chemical shifts of the 10-substituted methyleneanthrones with sigma+ constants is noted.
引用
收藏
页码:16 / 19
页数:4
相关论文
共 42 条
[1]   PARA-QUINONE METHIDE INITIATED INTRAMOLECULAR ELECTROPHILIC SUBSTITUTION-REACTIONS [J].
ANGLE, SR ;
LOUIE, MS ;
MATTSON, HL ;
YANG, WJ .
TETRAHEDRON LETTERS, 1989, 30 (10) :1193-1196
[2]   SYNTHESIS AND CHEMISTRY OF A QUINONE METHIDE MODEL FOR ANTHRACYCLINE ANTITUMOR ANTIBIOTICS [J].
ANGLE, SR ;
YANG, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4524-4528
[3]   O-17 NMR-SPECTROSCOPY - EFFECT OF SUBSTITUENTS ON CHEMICAL-SHIFTS FOR PARA-SUBSTITUTED BENZOIC-ACIDS, METHYL BENZOATES, CINNAMIC-ACIDS AND METHYL CINNAMATES [J].
BALAKRISHNAN, P ;
BAUMSTARK, AL ;
BOYKIN, DW .
ORGANIC MAGNETIC RESONANCE, 1984, 22 (12) :753-756
[4]  
BARNETT ED, 1926, CHEM BER, V59, P767
[5]  
Baumstark A. L., 1991, ADV OXYGENATED PROCE, VIII, P141
[6]  
BAUMSTARK AL, 1988, TETRAHEDRON LETT, P2143
[7]  
BAUMSTARK AL, 1990, TETRAHEDRON LETT, P957
[8]   FORMATION AND AUTOCATALYTIC DESTRUCTION OF THE QUINONE METHIDE FROM REDUCTIVE CLEAVAGE OF MENOGARIL [J].
BOLDT, M ;
GAUDIANO, G ;
HADDADIN, MJ ;
KOCH, TH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) :3330-3332
[9]  
Boykin D. W, 1991, 17O NMR SPECTROSCOPY
[10]   O-17 NMR-STUDIES ON ALKYL-SUBSTITUTED 1-TETRALONES - EFFECT OF TORSION ANGLE CHANGE AND REPULSIVE VANDERWAALS INTERACTIONS [J].
BOYKIN, DW ;
DEWPRASHAD, B ;
EISENBRAUN, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :425-429