Efficient synthesis of disulfides by air oxidation of thiols under sonication

被引:149
作者
Garcia Ruano, Jose Luis [1 ]
Parra, Alejandro [1 ]
Aleman, Jose [1 ]
机构
[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain
关键词
D O I
10.1039/b800705e
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
Alkyl, aryl and heteroaryl symmetrical disulfides can be easily obtained by heating the corresponding thiols for several hours at 80 degrees C with Et3N in DMF under atmospheric oxygen. These reactions are markedly accelerated by ultrasounds (few minutes at rt). Aromatic groups bearing electron donating and electron withdrawing groups, heteroaromatic, and alkyl thiols are analogously efficient affording disulfides in almost quantitative yields. Aminothiols and L-cysteine provide the corresponding disulfides without affecting the nitrogen function.
引用
收藏
页码:706 / 711
页数:6
相关论文
共 72 条
[61]
Oxidation of organic compounds by potassium permanganate supported on Montmorillonite k10 [J].
Shaabani, A ;
Bazgir, A ;
Lee, DG .
SYNTHETIC COMMUNICATIONS, 2004, 34 (19) :3595-3607
[62]
Solvent free permanganate oxidations [J].
Shaabani, A ;
Lee, DG .
TETRAHEDRON LETTERS, 2001, 42 (34) :5833-5836
[63]
2,6-Dicarboxypyridinium chlorochromate: an efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides [J].
Tajbakhsh, M ;
Hosseinzadeh, R ;
Shakoori, A .
TETRAHEDRON LETTERS, 2004, 45 (09) :1889-1893
[64]
TASADAQUE AS, 2003, TETRAHEDRON LETT, V44, P6789
[65]
OXIDATION OF THIOLS BY MOLECULAR OXYGEN IN TETRAMETHYLGUANIDINE [J].
WALLACE, TJ ;
JACOBSON, N ;
SCHRIESHEIM, A .
NATURE, 1964, 201 (491) :609-&
[66]
SOLVENT EFFECTS IN BASE-CATALYZED OXIDATION OF MERCAPTANS WITH MOLECULAR OXYGEN [J].
WALLACE, TJ ;
SCHRIESHEIM, A .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) :1514-&
[67]
BASE-CATALYZED OXIDATION OF MERCAPTANS .3. ROLE OF SOLVENT AND EFFECT OF MERCAPTAN STRUCTURE ON RATE DETERMINING STEP [J].
WALLACE, TJ ;
BARTOK, W ;
SCHRIESHEIM, A .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (05) :1311-&
[68]
Preparation of disulfides by the oxidation of thiols using bromine [J].
Wu, XM ;
Rieke, RD ;
Zhu, LS .
SYNTHETIC COMMUNICATIONS, 1996, 26 (01) :191-196
[69]
Conversion of thiols to disulfides using a hexamethylenetetramine-bromine complex [J].
Yavari, Issa ;
Rounaqi, Ali A. ;
Moradi, Loghman .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (11) :2659-2662
[70]
OXIDATION OF THIOLS BY DIMETHYL SULFOXIDE [J].
YIANNIOS, CN ;
KARABINOS, JV .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (11) :3246-&