Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions

被引:426
作者
Sato, K
Hyodo, M
Aoki, M
Zheng, XQ
Noyori, R [1 ]
机构
[1] Nagoya Univ, Dept Chem, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan
关键词
green chemistry; hydrogen peroxide; oxidation; phase-transfer catalyst; quaternary ammonium salts; sulfides; sulfones; sulfoxides;
D O I
10.1016/S0040-4020(01)00068-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aromatic and aliphatic sulfides are oxidized to sulfoxides or sulfones in high yield with 30% hydrogen peroxide under organic solvent- and halogen-free conditions. Dialkyl and alkyl aryl sulfides are cleanly oxidized to sulfoxides using aqueous hydrogen peroxide without catalysts. The best catalyst for the sulfone synthesis consists of sodium tungstate, phenylphosphonic acid, and methyltrioctyl-ammonium hydrogensulfate. Go-existing primary or secondary alcohol or olefinic moieties are unaffected under such conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2469 / 2476
页数:8
相关论文
共 78 条
[31]   A MILD, OSMIUM TETRAOXIDE-CATALYZED METHOD FOR THE OXIDATION OF SULFIDES TO SULFONES [J].
KALDOR, SW ;
HAMMOND, M .
TETRAHEDRON LETTERS, 1991, 32 (38) :5043-5046
[32]   UBER 2 EINFACHE, OPTISCH AKTIVE SULFOXYDE [J].
KARRER, P ;
ANTIA, NJ ;
SCHWYZER, R .
HELVETICA CHIMICA ACTA, 1951, 34 (05) :1392-1399
[33]   THE OXIDATION OF ORGANIC SUBSTANCES BY POTASSIUM PEROXYMONOSULFATE [J].
KENNEDY, RJ ;
STOCK, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (11) :1901-1906
[34]   An efficient oxidation of sulfides to sulfones using 2-methylpropanal and dioxygen [J].
Khanna, V ;
Maikap, GC ;
Iqbal, J .
TETRAHEDRON LETTERS, 1996, 37 (19) :3367-3370
[35]   Rapid oxidation of sulfides and sulfoxides with sodium hypochlorite [J].
Khurana, JM ;
Panda, AK ;
Ray, A ;
Gogia, A .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (02) :234-237
[36]   OXIDATION OF DIBENZOTHIOPHENE CATALYZED BY HEMOGLOBIN AND OTHER HEMOPROTEINS IN VARIOUS AQUEOUS-ORGANIC MEDIA [J].
KLYACHKO, NL ;
KLIBANOV, AM .
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 1992, 37 (01) :53-68
[37]   PERIODATE OXIDATION OF SULFIDES TO SULFOXIDES - SCOPE OF REACTION [J].
LEONARD, NJ ;
JOHNSON, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :282-&
[38]   SYNTHESIS OF SULFOXIDES BY OXIDATION OF THIOETHERS [J].
MADESCLAIRE, M .
TETRAHEDRON, 1986, 42 (20) :5459-5495
[39]  
MARCH J, 1992, ADV ORG CHEM, P1202
[40]   OXIDATION OF IMINES TO OXAZIRIDINES CATALYZED BY TRANSITION-METAL COMPLEXES USING MOLECULAR-OXYGEN AS THE TERMINAL OXIDANT [J].
MARTINY, L ;
JORGENSEN, KA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (06) :699-704