Facile oxygenation of organic sulfides with H2O2 catalyzed by Mn-Me3TACN compounds

被引:39
作者
Barker, JE [1 ]
Ren, T [1 ]
机构
[1] Univ Miami, Dept Chem, Coral Gables, FL 33146 USA
关键词
organic sulfide; catalytic oxygenation; Mn-Me(3)TACN; complexes; hydrogen peroxide;
D O I
10.1016/j.tetlet.2004.04.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two binuclear Mn-Me(3)TACN (Me(3)TACN is 1,4,7-N,N',N"-trimethyl-1,4,7-triazacyclononane) compounds catalyze the oxygenation of organic sulfides utilizing H2O2 under ambient conditions. Both phenyl sulfide and ethyl phenyl sulfide were converted to the corresponding sulfones and chloroethyl phenyl sulfide proceeds to its elimination product of phenyl vinyl sulfone. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4681 / 4683
页数:3
相关论文
共 28 条
[1]   Binuclear manganese complexes as catalysts in the selective and efficient oxidation of sulfides to sulfones [J].
Barton, DHR ;
Li, WG ;
Smith, JA .
TETRAHEDRON LETTERS, 1998, 39 (39) :7055-7058
[2]   Benzylic oxidation with H2O2 catalyzed by Mn complexes of N,N′,N"-trimethyl-1,4,7-triazacyclononane:: spectroscopic investigations of the active Mn species [J].
Bennur, TH ;
Sabne, S ;
Deshpande, SS ;
Srinivas, D ;
Sivasanker, S .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 185 (1-2) :71-80
[3]   Mn-trimethyltriazacyclononane/ascorbic acid: a remarkably efficient catalyst for the epoxidation of olefins and the oxidation of alcohols with hydrogen peroxide [J].
Berkessel, A ;
Sklorz, CA .
TETRAHEDRON LETTERS, 1999, 40 (45) :7965-7968
[4]   Catalytic aerobic oxidation of 2-chloroethyl ethylsulfide, a mustard simulant, under ambient conditions - Effect of solvents, ligands, and transition metals on reactivity [J].
Boring, E ;
Geletii, Y ;
Hill, CL .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 176 (1-2) :49-63
[5]   New ligands for manganese catalysed selective oxidation of sulfides to sulfoxides with hydrogen peroxide [J].
Brinksma, J ;
La Crois, R ;
Feringa, BL ;
Donnoli, MI ;
Rosini, C .
TETRAHEDRON LETTERS, 2001, 42 (24) :4049-4052
[6]   Oxidation of thioanisole by peroxomolybdate ions: direct oxygen transfer from tetraperoxomolybdate ion [J].
Bunton, CA ;
Gillitt, ND .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2002, 15 (01) :29-35
[7]   SULFIDE OXIDATION AND OXIDATIVE HYDROLYSIS OF THIOESTERS BY PEROXYMONOSULFATE ION [J].
BUNTON, CA ;
FOROUDIAN, HJ ;
KUMAR, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (01) :33-39
[8]   Oxidation of sulfide, phosphine, and benzyl substrates tethered to N-donor pyridine ligands in carboxylate-bridged diiron(II) complexes [J].
Carson, EC ;
Lippard, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3412-3413
[9]   Epoxidation of terminal or electron-deficient olefins with H2O2, catalysed by Mn-trimethyltriazacyclonane complexes in the presence of an oxalate buffer [J].
De Vos, DE ;
Sels, BF ;
Reynaers, M ;
Rao, YVS ;
Jacobs, PA .
TETRAHEDRON LETTERS, 1998, 39 (20) :3221-3224
[10]   Highly selective epoxidation of alkenes and styrenes with H2O2 and manganese complexes of the cyclic triamine 1,4,7-trimethyl-1,4,7-triazacyclononane [J].
DeVos, D ;
Bein, T .
CHEMICAL COMMUNICATIONS, 1996, (08) :917-918