Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source

被引:123
作者
Ando, T [1 ]
Minakata, S [1 ]
Ryu, I [1 ]
Komatsu, M [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 565, Japan
关键词
D O I
10.1016/S0040-4039(97)10553-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aziridination of alkenes proceeds successfully using Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide). When anhydrous Chloramine-T was added to an acetonitrile solution of alkenes in the presence of various CuCl catalysts and MS-5A, the corresponding aziridines were obtained in moderate to good yields. (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:309 / 312
页数:4
相关论文
共 21 条
  • [1] REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .9. NEW REAGENTS FOR AMINATION OF ETHYLENIC LINKAGE
    BARTON, DHR
    BRITTENKELLY, MR
    FERREIRA, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (09): : 1090 - 1100
  • [2] A NEW METHOD FOR THE PREPARATION OF (ARYLSULFONYLIMINOIODO)BENZENES
    BESENYEI, G
    NEMETH, S
    SIMANDI, LI
    [J]. TETRAHEDRON LETTERS, 1993, 34 (38) : 6105 - 6106
  • [3] BREMNER DH, 1985, SYNTHETIC REAGENTS, V6, P9
  • [4] CHLORAMINE-T AND RELATED N-HALOGEN-N-METALLO REAGENTS
    CAMPBELL, MM
    JOHNSON, G
    [J]. CHEMICAL REVIEWS, 1978, 78 (01) : 65 - 79
  • [5] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
    EVANS, DA
    FAUL, MM
    BILODEAU, MT
    ANDERSON, BA
    BARNES, DM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5328 - 5329
  • [6] COPPER-CATALYZED AZIRIDINATION OF OLEFINS BY (N-(PARA-TOLUENESULFONYL)IMINO)PHENYLIODINANE
    EVANS, DA
    FAUL, MM
    BILODEAU, MT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) : 6744 - 6746
  • [7] EVANS DA, 1994, J AM CHEM SOC, V116, P2742
  • [8] N-halocarbamate salts lead to more efficient catalytic asymmetric aminohydroxylation
    Li, GG
    Angert, HH
    Sharpless, KB
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24): : 2813 - 2817
  • [9] Catalytic asymmetric aminohydroxylation (AA) of olefins
    Li, GG
    Chang, HT
    Sharpless, KB
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04): : 451 - 454
  • [10] MECHANISM OF THE (DIIMINE)COPPER-CATALYZED ASYMMETRIC AZIRIDINATION OF ALKENES - NITRENE TRANSFER VIA LIGAND-ACCELERATED CATALYSIS
    LI, Z
    QUAN, RW
    JACOBSEN, EN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) : 5889 - 5890