Poly(N,N′-dichloro-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-Tetrachlorobenzene-1,3-disulfonamide as Novel Reagents for the Synthesis of N-Chloroamines, Nitriles and Aldehydes

被引:34
作者
Ghorbani-Vaghei, Ramin [1 ]
Veisi, Hojat [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan 65174, Iran
来源
SYNTHESIS-STUTTGART | 2009年 / 06期
关键词
TCBDA; PCBS; dichloroamines; nitriles; alcohols; NICKEL-CATALYZED OXIDATION; ONE-POT SYNTHESIS; PRIMARY AMINES; ORGANIC-SYNTHESIS; TETRABUTYLAMMONIUM PEROXYDISULFATE; CORRESPONDING NITRILES; PRIMARY ALCOHOLS; TERTIARY-AMINES; PRIMARY AMIDES; CONVERSION;
D O I
10.1055/s-0028-1087967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The applications of poly(N,N'-dichloro-N-ethylbenzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-tetrachlorobenzene-1,3-disulfonamide (TCBDA) as novel reagents for the preparation of N,N-dichloroamines, nitriles, and aldehydes from primary amines under various conditions are described. Also, a simple and effective procedure for the direct oxidative conversion of primary alcohols into nitriles was successfully carried Out with TCBDA and PCBS in aqueous ammonia.
引用
收藏
页码:945 / 950
页数:6
相关论文
共 35 条
[1]   THE CONVERSION OF PRIMARY AMINES TO CARBONYL COMPOUNDS BY A CHLOROMINE DEGRADATION [J].
BACHMANN, WE ;
CAVA, MP ;
DREIDING, AS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (21) :5554-5555
[2]   Reagents for organic synthesis: Use of organostannyl oxides as catalytic neutral agents in the preparation of nitriles from primary amides under microwave irradiation [J].
Bose, DS ;
Jayalakshmi, B .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1713-1714
[3]   Efficient one pot synthesis of Nitriles from Aldehydes in solid state using Peroxymonosulfate on Alumina [J].
Bose, DS ;
Narsaiah, AV .
TETRAHEDRON LETTERS, 1998, 39 (36) :6533-6534
[4]   A selective and mild oxidation of primary amines to nitriles with trichloroisocyanuric acid [J].
Chen, FE ;
Kuang, YY ;
Dai, HF ;
Lu, L ;
Huo, M .
SYNTHESIS-STUTTGART, 2003, (17) :2629-2631
[5]  
Chen FE, 2002, SYNTHESIS-STUTTGART, P1804
[6]   Tetrabutylammonium peroxydisulfate in organic synthesis. Part 8. An efficient and convenient nickel-catalyzed oxidation of primary amines to nitriles with tetrabutylammonium peroxydisulfate [J].
Chen, FE ;
Peng, ZZ ;
Fu, H ;
Liu, JD ;
Shao, LY .
JOURNAL OF CHEMICAL RESEARCH, 1999, (12) :726-727
[7]   Oxidative conversion of amines into their corresponding nitriles using o-iodoxybenzoic acid (IBX)/iodine:: Selective oxidation of aminoalcohols to hydroxynitriles [J].
Chiampanichayakul, Supanimit ;
Pohmakotr, Manat ;
Reutrakul, Vichai ;
Jaipetch, Thaworn ;
Kuhakarn, Chutima .
SYNTHESIS-STUTTGART, 2008, (13) :2045-2048
[8]  
CLARKE TG, 1968, TETRAHEDRON LETT, P5685
[9]   An insight of the reactions of amines with tirichloroisocyanuric acid [J].
De Luca, L ;
Giacomelli, G .
SYNLETT, 2004, (12) :2180-2184
[10]  
GAO S, 2001, SYNTHESIS-STUTTGART, P545