Dinitrogen tetroxide-impregnated charcoal (N2O4/charcoal):: Selective nitrosation of amines, amides, ureas, and thiols

被引:28
作者
Iranpoor, N [1 ]
Firouzabadi, H [1 ]
Pourali, AR [1 ]
机构
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran
关键词
dinitrogen tetroxide; nitrosamines; nitrosamides; nitrosothiols;
D O I
10.1081/SCC-200057999
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient N-nitrosation of amines, amides, and ureas, and also S-nitrosation of thiols were performed with dinitrogen tetroxide impregnated on activated charcoal (N2O4/charcoal) in CH2Cl2 at room temperature. High selectivity was observed for N-nitrosation of dialkyl amines, N-alkylamides and N-alkylureas. Dealkylation and N-nitrosation of trialkylamines were also performed by this reagent.
引用
收藏
页码:1517 / 1526
页数:10
相关论文
共 67 条
[1]   CATALYSIS BY CU2+ OF NITRIC-OXIDE RELEASE FROM S-NITROSOTHIOLS (RSNO) [J].
ASKEW, SC ;
BARNETT, DJ ;
MCANINLY, J ;
WILLIAMS, DLH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (04) :741-745
[2]  
BERENGUER R, 1989, SYNTHESIS-STUTTGART, P305
[3]   SELECTIVE CATALYSIS OF THIOETHER OXIDATIONS WITH DIOXYGEN - CRITICAL ROLE OF NITROSONIUM EDA COMPLEXES IN THE THERMAL AND PHOTOCHEMICAL TRANSFER OF OXYGEN-ATOM FROM NITROGEN-OXIDES TO SULFUR CENTERS [J].
BOSCH, E ;
KOCHI, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3172-3183
[4]   FREMYS SALT (POTASSIUM NITROSODISULFONATE) - A NITROSATING REAGENT FOR AMINES [J].
CASTEDO, L ;
RIGUERA, R ;
VAZQUEZ, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) :301-302
[5]   Studies on the intermolecular free radical addition of thionitrites to alkenes:: a convenient method for the preparation of α-tritylthio oximes and related derivatives [J].
Cavero, M ;
Motherwell, WB ;
Potier, P .
TETRAHEDRON LETTERS, 2001, 42 (26) :4377-4379
[6]   CHEMISTRY OF NITROSO-COMPOUNDS .12. MECHANISM OF NITROSATION AND NITRATION OF AQUEOUS PIPERIDINE BY GASEOUS DINITROGEN TETRAOXIDE AND DINITROGEN TRIOXIDE IN AQUEOUS ALKALINE-SOLUTIONS - EVIDENCE FOR THE EXISTENCE OF MOLECULAR ISOMERS OF DINITROGEN TETRAOXIDE AND DINITROGEN TRIOXIDE [J].
CHALLIS, BC ;
KYRTOPOULOS, SA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (12) :1296-1302
[7]   SYNTHESIS AND CHARACTERIZATION OF SOME NEW N-NITROSODIPEPTIDES [J].
CHALLIS, BC ;
MILLIGAN, JR ;
MITCHELL, RC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3103-3108
[8]   CHEMISTRY OF NITROSO-COMPOUNDS .11. NITROSATION OF AMINES BY THE 2-PHASE INTERACTION OF AMINES IN SOLUTION WITH GASEOUS OXIDES OF NITROGEN [J].
CHALLIS, BC ;
KYRTOPOULOS, SA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (02) :299-304
[9]  
CHANG SK, 1979, CANCER RES, V39, P3871
[10]   Heterolytic and homolytic Y-NO bond energy scales of nitroso-containing compounds: Chemical origin of NO release and NO capture [J].
Cheng, JP ;
Xian, M ;
Wang, K ;
Zhu, XQ ;
Yin, Z ;
Wang, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) :10266-10267