OXYGEN-TRANSFER PROCESSES TO SULFIDES AND SULFOXIDES MEDIATED BY CETYLPYRIDINIUM TETRAKIS(DIPEROXOMOLYBDO) PHOSPHATE

被引:10
作者
BALLISTRERI, FP [1 ]
TOMASELLI, GA [1 ]
TOSCANO, RM [1 ]
机构
[1] UNIV CATANIA,DIPARTIMENTO SCI CHIM,V A DORIA 6,I-95125 CATANIA,ITALY
来源
JOURNAL OF MOLECULAR CATALYSIS | 1991年 / 68卷 / 03期
关键词
D O I
10.1016/0304-5102(91)80085-H
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Oxidation of some aryl methyl sulfides and aryl methyl sulfoxides with hydrogen peroxide, mediated by cetylpyridinium tetrakis(diperoxomolybdo)phosphate (PCMP), was performed in chloroform/ethanol. In addition, the stoichiometric oxidation of sulfoxides to sulfones by PCMP was carried out in chloroform. Second-order rate laws, first order with respect to substrate and to PCMP, were observed in both catalytic and stoichiometric processes. Kinetic data seem to indicate that sulfides are oxidized by a bimolecular process which involves a nucleophilic attack of the substrate on the peroxidic oxygen. On the other hand, the possibility of radical incursion is suggested in the oxidation of sulfoxides.
引用
收藏
页码:269 / 275
页数:7
相关论文
共 27 条
[1]   THIANTHRENE 5-OXIDE AS MECHANISTIC PROBE IN OXYGEN-TRANSFER REACTIONS - THE CASE OF CARBONYL OXIDES VS DIOXIRANES [J].
ADAM, W ;
HAAS, W ;
SIEKER, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :5020-5022
[2]   EVIDENCE FOR A LINEAR SULFURANE INTERMEDIATE IN THE OXIDATION OF SULFOXIDE BY PERSULFOXIDE [J].
AKASAKA, T ;
ANDO, W .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (21) :1203-1204
[3]  
ALLISTRERI FP, IN PRESS J AM CHEM S
[4]   KINETICS AND MECHANISM OF THE TUNGSTEN-CATALYZED OXIDATION OF ORGANIC SULFIDES AND ALKENES BY HYDROGEN-PEROXIDE [J].
ARCORIA, A ;
BALLISTRERI, FP ;
TOMASELLI, GA ;
DIFURIA, F ;
MODENA, G .
JOURNAL OF MOLECULAR CATALYSIS, 1983, 18 (02) :177-188
[5]  
ARCORIA A, 1990, GAZZ CHIM ITAL, V120, P309
[6]   OPPOSITE REGIOSELECTIVITY IN THE EPOXIDATION OF GERANIOL AND LINALOOL WITH MOLYBDENUM AND TUNGSTEN PEROXO COMPLEXES [J].
ARCORIA, A ;
BALLISTRERI, FP ;
TOMASELLI, GA ;
DIFURIA, F ;
MODENA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2374-2376
[7]   PHASE-TRANSFER CATALYTIC-OXIDATION OF TERMINAL ALKYNES TO KETO ALDEHYDES BY DILUTE HYDROGEN-PEROXIDE [J].
BALLISTRERI, FP ;
FAILLA, S ;
TOMASELLI, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :830-831
[8]   A NEW FACILE SYNTHESIS OF ALPHA-DICARBONYL COMPOUNDS BY OXIDATION OF ALKYNES WITH MO(VI) PEROXOCOMPLEX PROMOTED BY MERCURIC ACETATE [J].
BALLISTRERI, FP ;
FAILLA, S ;
TOMASELLI, GA ;
CURCI, R .
TETRAHEDRON LETTERS, 1986, 27 (42) :5139-5142
[9]   OXIDATION OF ALKYNES CATALYZED BY MO(VI) AND W(VI) POLYOXOMETALATES [J].
BALLISTRERI, FP ;
FAILLA, S ;
SPINA, E ;
TOMASELLI, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :947-949
[10]  
BALLISTRERI FP, 1988, ROLE OXYGEN CHEM BIO, P341