Oxidative N-nitration of secondary amines

被引:0
|
作者
O. V. Anikin
G. V. Pokhvisneva
D. L. Lipilin
A. V. Mezhenin
V. A. Tartakovsky
机构
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源
Russian Chemical Bulletin | 2009年 / 58卷
关键词
secondary amines; nitrites; diacetoxyiodobenzene; oxidative nitration; -nitroamines; -nitrosoamines;
D O I
暂无
中图分类号
学科分类号
摘要
Reaction of secondary amines with the nitrite anion assisted by diacetoxyiodobenzene results in respective N-nitroamines. It is the first example of oxidative nitration of the amino group. N-Nitrosoamines are by-products. The yields and the ratio of the nitration and nitrosation products depend on the nature of the starting amine, cation of the salt used, and the solvent.
引用
收藏
页码:2043 / 2046
页数:3
相关论文
共 50 条
  • [41] N-NITRATION OF 5-AMINOTETRAZOLE WITH TETRANITROMETHANE, HEXANITROETHANE AND TETRANITRATE OF PENTAERYTHRITE
    MAYANTS, AG
    PYRESEVA, KG
    GORDEICHUK, SS
    ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (04): : 884 - 887
  • [42] N-NITRATION OF AMIDES .5. NITRATION OF PRIMARY CARBOXAMIDES BY NITRONIUM TETRAFLUOROBORATE IN A MEDIUM OF ORGANIC-SOLVENTS
    ANDREEV, SA
    LEBEDEV, BA
    TSELINSKII, IV
    ZHURNAL ORGANICHESKOI KHIMII, 1978, 14 (12): : 2513 - 2516
  • [43] N-NITRATION OF AMIDES .6. MECHANISM OF NITROLYSIS OF N,N-DIALKYL CARBOXAMIDES BY NITRONIUM TETRAFLUOROBORATE IN ACETONITRILE
    ANDREEV, SA
    LEBEDEV, BA
    TSELINSKII, IV
    SHOKHOR, IN
    ZHURNAL ORGANICHESKOI KHIMII, 1980, 16 (07): : 1353 - 1360
  • [44] N-nitration, N-15-labeling, and N-to-N linking of hydroxyl-silylated pyrimidine nucleosides
    Ariza, X
    Farras, J
    Serra, C
    Vilarrasa, J
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05): : 1547 - 1549
  • [45] NITRATION BY NITRONIUM SALTS .1. NITRATION OF SECONDARY-AMINES BY NITRONIUM SALTS
    ILYUSHIN, MA
    GOLOD, EL
    GIDASPOV, BV
    ZHURNAL ORGANICHESKOI KHIMII, 1977, 13 (01): : 11 - 17
  • [46] A CONVENIENT METHOD FOR N-NITRATION USING AMMONIUM-NITRATE TRIFLUOROACETIC-ANHYDRIDE
    SURI, SC
    CHAPMAN, RD
    SYNTHESIS-STUTTGART, 1988, (09): : 743 - 745
  • [47] N-NITRATION OF AMIDES .7. NITROLYSIS KINETICS OF N,N-DIALKYL CARBOXAMIDES BY NITRONIUM TETRAFLUOROBORATE IN ACETONITRILE
    ANDREEV, SA
    LEBEDEV, BA
    TSELINSKII, IV
    ZHURNAL ORGANICHESKOI KHIMII, 1980, 16 (07): : 1360 - 1365
  • [48] Iodine-mediated oxidative N-N coupling of secondary amines to hydrazines
    Ren, Linning
    Wang, Manman
    Fang, Benyao
    Yu, Wenquan
    Chang, Junbiao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (13) : 3446 - 3450
  • [49] Synthesis of beta-aminosulfonopeptides activated through selective N-nitration of a taurine amide unit
    Paik, S
    White, EH
    TETRAHEDRON LETTERS, 1996, 37 (27) : 4663 - 4666
  • [50] CATALYZED NITRATION OF AMINES .2. RELATIVE BASICITIES OF SECONDARY AMINES IN ACETIC ACID
    DUNN, GE
    MACKENZIE, JC
    WRIGHT, GF
    CANADIAN JOURNAL OF RESEARCH SECTION B-CHEMICAL SCIENCES, 1948, 26 (01): : 104 - 113