New insights into N-tert-butyl-alpha-phenylnitrone (PBN) as a spin trap .2. the reactivity of PBN and 5,5-dimethyl-4,5-dihydropyrrole N-oxide (DMPO) toward N-heteroaromatic bases

被引:29
作者
Alberti, A
Carloni, P
Eberson, L
Greci, L
Stipa, P
机构
[1] LUND UNIV,DEPT CHEM,S-22100 LUND,SWEDEN
[2] CNR,ICOCEA,AREA RIC,I-40129 BOLOGNA,ITALY
[3] UNIV ANCONA,DIPARTIMENTO SCI MAT & TERRA,I-60131 ANCONA,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1997年 / 05期
关键词
D O I
10.1039/a608004i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of N-tert-butyl-alpha-phenylnitrone (PEN) and 5,5-dimethyl-4,5-dihydropyrroline N-oxide (DMPO) with a series of N-heteroaromatic bases have been studied in different solvents (benzene, dichloromethane, acetonitrile) in the presence of such oxidants as PbO2, chloranil and tetrabutylammonium dodecatungstocobalt(III)ate. In all cases spin adducts were formed and their corresponding EPR signals were recorded, The formation of the spin adducts, which mostly involves nucleophilic addition of a base to the nitrone and subsequent oxidation (Forrester-Hepburn mechanism) is also discussed and compared to conventional spin trapping and to 'inverted spin trapping', In order to obtain further evidence for the mechanism involved some reactions were carried out using other oxidants, such as galvinoxyl and 2,2-diphenyl-1-picrylhydrazyl (DPPH), The reaction mechanisms are discussed on the basis of the redox potentials of the studied nucleophiles, Particular attention is given to the benzotriazolyl-DMPO. spin adduct, whose generation and decay rates were determined in the presence of some benzoquinones having different redox potentials.
引用
收藏
页码:887 / 892
页数:6
相关论文
共 46 条
[1]  
ALBERTI A, 1987, TETRAHEDRON, V43, P3031
[2]  
ANDRUZZI R, 1979, ANN CHIM-ROME, V69, P583
[3]   USE OF A NEW PULSED SOLID ELECTRODE IN STUDY OF REDOX PROCESSES BY ALTERNATING-CURRENT VOLTAMMETRY [J].
ANDRUZZI, R ;
TRAZZA, A .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1978, 90 (03) :389-397
[4]  
ANDRUZZI R, 1977, J ELECTROANAL CHEM, V77, P101, DOI 10.1016/S0022-0728(77)80323-9
[5]   SIDE-CHAIN OXIDATION OF ALPHA-SUBSTITUTED 4-METHOXYTOLUENES BY POTASSIUM 12-TUNGSTOCOBALT(III)ATE - THE EFFECT OF ALPHA-SUBSTITUENTS ON THE FORMATION AND DEPROTONATION OF THE INTERMEDIATE CATION RADICALS [J].
BACIOCCHI, E ;
BIETTI, M ;
MATTIOLI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7106-7110
[6]   Reactivity of [(CoW12O40)-W-III](5-) with organic radicals in aqueous solution. Evidence for an electron transfer mechanism [J].
Baciocchi, E ;
Bietti, M ;
Steenken, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (07) :1261-1263
[7]   A KINETIC-STUDY OF THE ELECTRON-TRANSFER-INITIATED CARBON SILICON BOND-CLEAVAGE REACTIONS OF BENZYLTRIALKYLSILANES PROMOTED BY 12-TUNGSTOCOBALT(III)ATE ION [J].
BACIOCCHI, E ;
CRESCENZI, M ;
FASELLA, E ;
MATTIOLI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4684-4689
[8]   SYNTHESIS AND REACTIVITY WITH ORGANOMETALLIC REAGENTS OF BENZIMIDAZOLE N-OXIDES [J].
BERTI, C ;
COLONNA, M ;
GRECI, L ;
MARCHETTI, L .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (01) :17-19
[9]   NEW ASPECTS IN THE CHLORINATION OF INDOLES WITH 1-CHLOROBENZOTRIAZOLE AND 1-CHLOROISATIN [J].
BERTI, C ;
GRECI, L ;
ANDRUZZI, R ;
TRAZZA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) :4895-4899
[10]  
BIETTI M, 1996, J CHEM SOC CHEM COMM, P1307