A facile noncatalytic pathway for the nitrene transfer process: expeditious access to aziridines

被引:45
作者
Saikia, Indranirekha [1 ]
Kashyap, Bishwapran [1 ]
Phukan, Prodeep [1 ]
机构
[1] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India
关键词
PORPHYRIN-CATALYZED AZIRIDINATION; NITROGEN-ATOM-TRANSFER; EFFICIENT AZIRIDINATION; BROMAMINE-T; BOND FORMATION; CHLORAMINE-T; N BOND; OLEFINS; ALKENES; AMIDATION;
D O I
10.1039/c0cc05387b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A fast and efficient method has been developed for generation of sulfonyl nitrene from N,N-dibromo-p-toluenesulfonamide (TsNBr2) in the presence of a base without any catalyst. This method was applied to produce aziridines from different kinds of olefins within a short time in high yields.
引用
收藏
页码:2967 / 2969
页数:3
相关论文
共 64 条
[1]   A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T trihydrate [J].
Albone, DP ;
Aujla, PS ;
Taylor, PC ;
Challenger, S ;
Derrick, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9569-9571
[2]   Pyridinium hydrobromide perbromide: A versatile catalyst for aziridination of olefins using Chloramine-T [J].
Ali, SI ;
Nikalje, MD ;
Sudalai, A .
ORGANIC LETTERS, 1999, 1 (05) :705-707
[3]   CYANONITRENE . REACTION WITH SATURATED HYDROCARBONS [J].
ANASTASSIOU, AG ;
SIMMONS, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3177-+
[4]   Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source [J].
Ando, T ;
Minakata, S ;
Ryu, I ;
Komatsu, M .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :309-312
[5]   Palladium(II)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent [J].
Antunes, AMM ;
Marto, SJL ;
Branco, PS ;
Prabhakar, S ;
Lobo, AM .
CHEMICAL COMMUNICATIONS, 2001, (05) :405-406
[6]   Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study [J].
Au, SM ;
Huang, JS ;
Yu, WY ;
Fung, WH ;
Che, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9120-9132
[7]   PRESSURE-INDUCED SYNTHESIS OF AN N-SULFONYL-1H-AZEPINE BY SULFONYL-NITRENE INSERTION INTO BENZENE [J].
AYYANGAR, NR ;
BAMBAL, RB ;
LUGADE, AG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (15) :790-791
[8]   NITRENES [J].
BELLOLI, R .
JOURNAL OF CHEMICAL EDUCATION, 1971, 48 (07) :422-&
[9]   Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate [J].
Catino, AJ ;
Nichols, JM ;
Forslund, RE ;
Doyle, MP .
ORGANIC LETTERS, 2005, 7 (13) :2787-2790
[10]   Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene [J].
Chanda, BM ;
Vyas, R ;
Bedekar, AV .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :30-34