Electrochemical synthesis of isocyanides and 1,n-diisocyanides

被引:0
|
作者
Hess, U
Brosig, H
Komenda, J
机构
[1] Humboldt Univ, Inst Pharmazie, Berlin, Germany
[2] Masaryk Univ, Inst Theoret & Phys Chem, CS-60177 Brno, Czech Republic
来源
PHARMAZIE | 1999年 / 54卷 / 06期
关键词
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Some isocyanide structures have shown fungicide, antibiotic, insecticide, akarizide and other biological activities. Electrochemical reduction of substituted tosylmethylisocyanides (TosMICs) in acetonitrile/0,1 M tetraalkylammonium supporting-electrolyte at Hg-electrodes led to new alkyl-, aryl and 1,n-diisocyanides in good yields. The reaction proceeds in a two-electron C,S-cleavage, reducing exclusively the tosyl-function. The high selectivity of the corresponding ECE-mechanism is supported by quantum-chemical calculation.
引用
收藏
页码:412 / 417
页数:6
相关论文
共 50 条
  • [41] SYNTHESIS OF ISOCYANIDES FROM N-MONOSUBSTITUTED FORMAMIDES, PHOSPHANES, AND AZODICARBOXYLIC ACID DERIVATIVES
    BEIJER, B
    UGI, I
    VONHINRI.E
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (10) : 929 - &
  • [42] S-alkyl Dithiocarbamates Synthesis through Electrochemical Multicomponent Reaction of Thiols, Hydrogen Sulfide, and Isocyanides
    Liu, Xiaoying
    Cai, Tian-cheng
    Zhu, Mengxue
    Liu, Yuxuan
    Xia, Jingjing
    Xie, Junyan
    Wen, Lixin
    Gui, Qing-Wen
    Yin, Yulong
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12311 - 12318
  • [43] Electrochemical Benzylic C-H Functionalization with Isocyanides
    Tang, Shanyu
    Guillot, Regis
    Grimaud, Laurence
    Vitale, Maxime R.
    Vincent, Guillaume
    ORGANIC LETTERS, 2022, 24 (11) : 2125 - 2130
  • [44] Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis
    Kim, Jungwon
    Hong, Soon Hyeok
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [45] Metal-free electrochemical synthesis of α-ketoamides via decarboxylative coupling of α-keto acids with isocyanides and water
    Zhao, Feng
    Meng, Na
    Sun, Ting
    Wen, Jiangwei
    Zhao, Xiaohui
    Wei, Wei
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (23): : 6508 - 6514
  • [46] Reaction between isocyanides and N,N′-dimethylbarbituric acid.: Synthesis of push-pull olefinic systems
    Yavari, I
    Hazeri, N
    Maghsoodlou, MT
    Moradi, A
    JOURNAL OF CHEMICAL RESEARCH, 2001, (07) : 272 - 273
  • [48] Straightforward Synthesis of Chiral Hydroxy Isocyanides
    Bauer, Michael
    Kazmaier, Uli
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (14) : 2360 - 2366
  • [49] Multicomponent reactions of isocyanides in the synthesis of heterocycles
    Ivachtchenko, A. V.
    Ivanenkov, Ya A.
    Kysil, V. M.
    Krasavin, M. Yu
    Ilyin, A. P.
    RUSSIAN CHEMICAL REVIEWS, 2010, 79 (09) : 787 - 817
  • [50] Recent application of isocyanides in synthesis of heterocycles
    Sadjadi, Samahe
    Heravi, Majid M.
    TETRAHEDRON, 2011, 67 (15) : 2707 - 2752