OXIDATION OF N-ALKYLAMIDES TO NOVEL HYDROPEROXIDES BY DIOXYGEN

被引:68
作者
DRAGO, RS
RILEY, R
机构
[1] Department of Chemistry, University of Florida, Gainesville
关键词
D O I
10.1021/ja00157a034
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the facile, uncatalyzed, oxidation of 1 -methyl-2-pyrrolidinone by 02 at 75 °C and 3 atm pressure. Approximately 2 M concentrations of an oxidizing agent are formed in the neat solvent, dept and apt l3C NMR as well as mass spectral analysis indicate that 5-hydroperoxo-1 -methyl-2-pyrrolidinone is formed. The hydroperoxide is converted to 1 -methylsuccinimide by peroxide decomposition catalysts. © 1990, American Chemical Society. All rights reserved.
引用
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页码:215 / 218
页数:4
相关论文
共 34 条
[1]   4A-HYDROPEROXYFLAVIN N-OXIDATION OF TERTIARY-AMINES [J].
BALL, S ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) :4017-4019
[2]  
BARNETT G H, 1973, Tetrahedron Letters, V30, P2887
[3]  
BASOLO F, 1978, J AM CHEM SOC, V100, P4416
[4]   ELECTROPHILIC OXYGEN-ATOM TRANSFER CHEMISTRY OF ALPHA-AZOHYDROPEROXIDES [J].
BAUMSTARK, AL .
BIOORGANIC CHEMISTRY, 1986, 14 (03) :326-343
[5]  
BOUSCHER LL, 1970, J AM CHEM SOC, V92, P2725
[6]  
BRUICE TC, 1988, J AM CHEM SOC, V110, P158
[7]  
BRUICE TC, 1982, J AM CHEM SOC, V104, P6123
[8]   EPOXIDATION OF OLEFINS BY CYTOCHROME-P-450 MODEL COMPOUNDS - KINETICS AND STEREOCHEMISTRY OF OXYGEN ATOM TRANSFER AND ORIGIN OF SHAPE SELECTIVITY [J].
COLLMAN, JP ;
BRAUMAN, JI ;
MEUNIER, B ;
HAYASHI, T ;
KODADEK, T ;
RAYBUCK, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2000-2005
[9]   PROBING STRUCTURE-FUNCTION RELATIONS IN HEME-CONTAINING OXYGENASES AND PEROXIDASES [J].
DAWSON, JH .
SCIENCE, 1988, 240 (4851) :433-439
[10]  
DEMONTELLANO PRO, 1985, CYTOCHROME P 450