A convenient method for production of thionitrites and disulfides under mild and heterogeneous condition

被引:42
作者
Zolfigol, MA [1 ]
机构
[1] Bu Ali Sina Univ, Coll Sci, Dept Chem, Hamadan 65174, Iran
关键词
D O I
10.1080/00397910008087194
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thiols can be readily converted to their corresponding thionitrite with a combination of inorganic acidic salts and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.
引用
收藏
页码:1593 / 1597
页数:5
相关论文
共 13 条
[1]   Reversibility of S-nitrosothiol formation [J].
Beloso, PH ;
Williams, DLH .
CHEMICAL COMMUNICATIONS, 1997, (01) :89-90
[2]   CLAY-SUPPORTED REAGENTS .4. A NOVEL COUPLING OF THIOLS INTO DISULFIDES, VIA THIONITRITE INTERMEDIATES USING A CLAY-SUPPORTED NITROSATION REAGENT [J].
CORNELIS, A ;
DEPAYE, N ;
GERSTMANS, A ;
LASZLO, P .
TETRAHEDRON LETTERS, 1983, 24 (30) :3103-3106
[3]   Selective and efficient transformation of thioethers to their sulfoxides and catalytic conversions of thiols to the disulfides with hydrated iron(III) and copper(II) nitrates in aprotic organic solvents or under solvent free conditions. [J].
Firouzabadi, H ;
Iranpoor, N ;
Zolfigol, MA .
SYNTHETIC COMMUNICATIONS, 1998, 28 (07) :1179-1187
[4]   In vivo aspects of nitric oxide (NO) chemistry: Does peroxynitrite (-OONO) play a major role in cytotoxicity? [J].
Fukuto, JM ;
Ignarro, LJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (04) :149-152
[5]   Dinitrogen tetroxide copper nitrate complex [Cu(NO3)2.N2O4] as a new nitrosating agent for catalytic coupling of thiols via thionitrite [J].
Iranpoor, N ;
Firouzabadi, H ;
Zolfigol, MA .
SYNTHETIC COMMUNICATIONS, 1998, 28 (02) :367-375
[6]  
KEEFER L. K., 1996, METHODS NITRIC OXIDE, P509
[7]   NEW SIMPLE SYNTHESES OF UNSYMMETRICAL DISULFIDES AND THIOLSULFONATES [J].
OAE, S ;
KIM, YH ;
FUKUSHIMA, D ;
TAKATA, T .
CHEMISTRY LETTERS, 1977, (08) :893-896
[8]   Nitric oxide release from S-nitrosothiols (RSNO) - The role of copper ions [J].
Williams, DLH .
TRANSITION METAL CHEMISTRY, 1996, 21 (02) :189-191
[9]  
WILLIAMS DLH, 1996, SUPPLEMENT F2 CHEM A, P665
[10]   Efficient and chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions with sodium nitrite and oxalic acid two hydrate [J].
Zolfigol, MA .
SYNTHETIC COMMUNICATIONS, 1999, 29 (06) :905-910