Silica phosphoric acid/NaNO2 as a novel heterogeneous system for the coupling of thiols to their corresponding disulfides

被引:49
作者
Zolfigol, MA
Shirini, F
Zamani, K
Ghofrani, E
Ebrahimi, S
机构
[1] Bu Ali Sina Univ, Coll Sci, Chem Dept, Hamadan 65174, Iran
[2] Gilan Univ, Coll Sci, Dept Chem, Rasht, Iran
[3] Arak Univ, Coll Sci, Chem Dept, Arak, Iran
关键词
disulfides; silica chloride; silica phosphoric acid; thiols; thionitrites (S-nitrosothiols);
D O I
10.1080/10426500490474842
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Silica phosphoric acid was prepared vis reaction of silica chloride (I) and phosphoric acid. Thiols can be readily converted to their corresponding thionitrites with a combination of silica phosphoric acid (II), wet Sio(2), 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:2177 / 2182
页数:6
相关论文
共 34 条
[1]  
Amado S., 1998, J CHEM SOC P2, P1869
[2]   Reversibility of S-nitrosothiol formation [J].
Beloso, PH ;
Williams, DLH .
CHEMICAL COMMUNICATIONS, 1997, (01) :89-90
[3]   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
[4]   Formation of peroxynitrite from S-nitrosothiols and hydrogen peroxide [J].
Coupe, PJ ;
Williams, DLH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (06) :1057-1058
[5]   Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane [J].
Demir, AS ;
Igdir, AC ;
Mahasneh, AS .
TETRAHEDRON, 1999, 55 (42) :12399-12404
[6]  
DROY B, 1994, J ORG CHEM, V59, P7019
[7]   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
[8]  
Firouzabadi H, 2000, SYNLETT, P263
[9]   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
[10]   Mechanism of the nitrosation of thiols and amines by oxygenated center dot NO solutions: The nature of the nitrosating intermediates [J].
Goldstein, S ;
Czapski, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) :3419-3425