A free radical process for oxidation of hydrocarbons promoted by nonmetal xanthone and tetramethylammonium chloride under mild conditions

被引：30

作者：

Du, Zhongtian ^{[1
,2
]}

Sun, Zhiqiang ^{[1
]}

Zhang, Wei ^{[1
]}

Miao, Hong ^{[1
]}

Ma, Hong ^{[1
]}

Xu, Jie ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 15期

关键词：

Aerobic oxidation; Hydrocarbons; Xanthone; Nitroxyl radical; Quaternary ammonium salts; N-HYDROXYPHTHALIMIDE NHPI; QUATERNARY AMMONIUM-SALTS; MOLECULAR-OXYGEN; AEROBIC OXIDATION; METAL-FREE; HYDROGEN ABSTRACTION; CATALYTIC-OXIDATION; ELECTRON-TRANSFER; HIGHLY EFFICIENT; ONIUM SALTS;

D O I：

10.1016/j.tetlet.2009.01.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nonmetal catalytic system consisting of N-hydroxyphthalimide, xanthone, and tetramethylammonium chloride was developed. A wide range of hydrocarbons could be oxidized efficiently with dioxygen under mild conditions. In the presence of xanthone and tetramethylammonium chloride, catalytic activity of N-hydroxyphthalimide was greatly improved, and selectivity for alkyl hydroperoxide was remarkably decreased. (C) 2009 Published by Elsevier Ltd.

引用

页码：1677 / 1680

页数：4

共 36 条

[1] Hydroxylamines as oxidation catalysts: Thermochemical and kinetic studies [J].

Amorati, R ;

Lucarini, M ;

Mugnaini, V ;

Pedulli, GF ;

Minisci, F ;

Recupero, F ;

Fontana, F ;

Astolfi, P ;

Greci, L .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1747-1754

[2] Synthesis of naphthalenediols by aerobic oxidation of diisopropylnaphthalenes catalyzed by N-hydroxyphthalimide (NHPI)/α,α′-azobisisobutyronitrile (AIBN) [J].

Aoki, Y ;

Sakaguchi, S ;

Ishii, Y .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :199-202

[3] Selective catalytic oxidation of cyclohexylbenzene to cyclohexylbenzene-1-hydroperoxide:: a coproduct-free route to phenol [J].

Arends, IWCE ;

Sasidharan, M ;

Kühnle, A ;

Duda, M ;

Jost, C ;

Sheldon, RA .

TETRAHEDRON, 2002, 58 (44) :9055-9061

[4] An experimental and theoretical study of the catalytic effect of quaternary ammonium salts on the oxidation of hydrocarbons [J].

Barrio, L ;

Toribio, PP ;

Campos-Martin, JM ;

Fierro, JLG .

TETRAHEDRON, 2004, 60 (50) :11527-11532

[5] Oxidation of hydrocarbons by O2 in the presence of onium salts and onium ion-pair complexes as catalysts [J].

Csányi, LJ ;

Jáky, K ;

Kóta, Z ;

Páli, T .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 209 (1-2) :59-68

[6] The role of onium salts in the oxidation of hydrocarbons by O2 catalysed by cationic phase-transfer reagents [J].

Csányi, LJ ;

Jáky, K ;

Pálinkó, I ;

Rockenbauer, A ;

Korecz, L .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2000, 2 (17) :3801-3805

[7] Oxidation of organic substrates by molecular oxygen mediated by N-hydroxyphthalimide (NHPI) and acetaldehyde [J].

Einhorn, C ;

Einhorn, J ;

Marcadal, C ;

Pierre, JL .

CHEMICAL COMMUNICATIONS, 1997, (05) :447-448

[8] Aerobic oxidation of alcohols and alkylaromatics with dioxygen catalysed by N-hydroxyphthalimide with vanadium co-catalysts [J].

Figiel, P. J. ;

Sobczak, J. M. .

NEW JOURNAL OF CHEMISTRY, 2007, 31 (09) :1668-1673

[9] New efficient aerobic oxidation of some alcohols with dioxygen catalysed by N-hydroxyphtalimide with vanadium co-catalysts [J].

Figiel, PJ ;

Sobczak, JM ;

Ziólkowski, JJ .

CHEMICAL COMMUNICATIONS, 2004, (02) :244-245

[10]

Figiel PJ, 2001, POL J CHEM, V75, P869

← 1 2 3 4 →