ELECTROCHEMICAL-BEHAVIOR OF C-METHOXY, AMINO, CYANO, AND MERCAPTO NITRONES

被引:10
作者
ACKEN, BJ [1 ]
GALLIS, DE [1 ]
WARSHAW, JA [1 ]
CRIST, DR [1 ]
机构
[1] GEORGETOWN UNIV,DEPT CHEM,WASHINGTON,DC 20057
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1992年 / 70卷 / 07期
关键词
D O I
10.1139/v92-263
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The redox behavior of various C-substituted nitrones was investigated by cyclic voltammetry in acetonitrile. These included C-methoxynitrones (MeO)CR = N(O)t-Bu with R = C6H5(1a), p-MeOC6H4 (1b), p-NO2C6H4 (1c), and H (1d) and nitrones YCH = N(O)t-Bu with Y = n-BuS (2a), CN (2b), and C6H5NH (2c). All gave anodic peaks which can be identified as oxidations of the nitrone function. Controlled potential electrolysis of la at 1.05 V (SCE) showed that its oxidation was a one-electron process. Reduction of la occurs stepwise at -2.08 and at -2.47 V, the same potential for reduction of methyl N-tert-butylbenzimidate (MeO)CPh = Nt-Bu. With electrochemical windows of ca. 3 V, all of the nitrones studied appear suitable for spin-trapping experiments.
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页码:2076 / 2080
页数:5
相关论文
共 31 条
[1]   ACYCLIC ALPHA-ALKOXYNITRONES - A NEW CLASS OF SPIN-TRAPPING AGENTS [J].
ACKEN, BJ ;
WARSHAW, JA ;
GALLIS, DE ;
CRIST, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1743-1745
[2]   DIMERIZATION, DISPROPORTIONATION AND ECE MECHANISMS IN REDUCTION OF IMINES IN ACETONITRILE AND DIMETHYL-FORMAMIDE [J].
ANDRIEUX, CP ;
SAVEANT, JM .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1971, 33 (02) :453-&
[3]  
BAIZER MM, 1983, ORGANIC CHEM, P639
[4]   APPLICATION OF SPIN TRAPPING TO DETECTION OF RADICAL INTERMEDIATES IN ELECTROCHEMICAL TRANSFORMATIONS [J].
BARD, AJ ;
GILBERT, JC ;
GOODIN, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (02) :620-621
[5]  
BARD AJ, 1980, ELECTROCHEMICAL METH, P222
[6]  
Breuer E., 1989, NITRONES NITRONATES, P139
[7]   A NITRONE-BASED CYCLOADDITION APPROACH TO THE SYNTHESIS OF THE GLYCOSYL SYSTEM OF NOGALOMYCIN, MENOGARIL, AND THEIR CONGENERS [J].
DESHONG, P ;
LI, W ;
KENNINGTON, JW ;
AMMON, HL ;
LEGINUS, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1364-1373
[8]   STERICALLY HINDERED REACTIONS OF GRIGNARD REAGENTS WITH SCHIFF BASES [J].
EMLING, BL ;
HORVATH, RJ ;
SARACENO, AJ ;
ELLERMEYER, EF ;
HAILE, L ;
HUDAC, LD .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (05) :657-660
[9]   ALKOXYOXAZIRIDINES - STEREOCHEMICAL ASPECTS OF IMIDATE OXIDATION, AN ASYMMETRIC-SYNTHESIS, AND UNUSUALLY FACILE E-Z ISOMERIZATIONS [J].
GONZALEZ, O ;
GALLIS, DE ;
CRIST, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3266-3270
[10]   ANODIC-OXIDATION PATHWAYS OF N-ALKYLANILINES [J].
HAND, RL ;
NELSON, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (03) :850-860