Liquid-phase oxidation of sulfides by an aluminum (and titanium) tert-butoxide-tert-butyl hydroperoxide system

被引:7
作者
Dodonov, VA [1 ]
Zaburdaeva, EA [1 ]
Stepovik, LP [1 ]
机构
[1] NI Lobachevskii State Univ, Nizhnii Novgorod 603950, Russia
关键词
sulfides; sulfones; aluminum and titanium tert-butoxides; tert-butyl hydroperoxide; oxidation; metal-containing trioxides; electron-excited dioxygen;
D O I
10.1007/s11172-005-0026-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A system aluminum (and titanium) tert-butoxide-tert-butyl hydroperoxide (I : 2) under mild conditions (20degreesC, 1h) oxidizes aliphatic and alkylaromatic sulfides and diphenyl sulf-ide to the corresponding sulfones in yields close to similar to100%. The oxidation is induced by electronexcited dioxygen formed upon thermal decomposition of intermediate metal-containing peroxy trioxides (ozonides). The latter are formed as a result of the reversible reaction of aluminum or titanium tert-butoxides with tert-butyl hydroperoxide followed by the interaction of di-tertbutoxy-tert-butylperoxyaluminum and tri-tert-butoxy-tert-butylperoxytitanium that formed with another (BuOOH)-O-t molecule. Aluminum-containing peroxide ((BuO)-O-t)(2)AlOOBut oxidizes sulfides to sulfoxides.
引用
收藏
页码:1729 / 1734
页数:6
相关论文
共 27 条
[11]  
Eichhorn G. L, 1973, INORGANIC BIOCH, V1
[12]   THE VIBRATIONAL SPECTRA OF SULFONES [J].
FEAIRHELLER, WR ;
KATON, JE .
SPECTROCHIMICA ACTA, 1964, 20 (07) :1099-1108
[13]   CHEMISTRY OF SINGLET OXYGEN .14. REACTIVE INTERMEDIATE IN SULFIDE PHOTOOXIDATION [J].
FOOTE, CS ;
PETERS, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (15) :3795-&
[14]  
HASLAM JH, 1954, Patent No. 2684972
[15]  
KARAULOVA EN, 1959, ZH OBSHCH KHIM+, V29, P3033
[16]   CHEMISTRY OF SINGLET OXYGEN .45. MECHANISM OF THE PHOTO-OXIDATION OF SULFIDES [J].
LIANG, JJ ;
GU, CL ;
KACHER, ML ;
FOOTE, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) :4717-4721
[17]   SYNTHESIS OF SULFOXIDES BY OXIDATION OF THIOETHERS [J].
MADESCLAIRE, M .
TETRAHEDRON, 1986, 42 (20) :5459-5495
[18]  
MARTYNOVA IM, 2001, H OBSHCH KHIM, V71, P1681
[19]   THE PREPARATION AND PROPERTIES OF SULFUR COMPOUNDS RELATED TO PETROLEUM .1. THE DIALKYL SULFIDES AND DISULFIDES [J].
MCALLAN, DT ;
CULLUM, TV ;
DEAN, RA ;
FIDLER, FA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (08) :3627-3632
[20]   STRUCTURES AND ENERGIES OF INTERMEDIATES IN THE REACTIONS OF SINGLET OXYGEN WITH ORGANIC PHOSPHINES AND SULFIDES [J].
NAHM, K ;
LI, Y ;
EVANSECK, JD ;
HOUK, KN ;
FOOTE, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4879-4884