Heterospin biradicals based on new piperidineoxyl-substituted 3,6-di-tert-butyl-o-benzoquinone

被引：0
|
作者：
E. N. Egorova
N. O. Druzhkov
K. A. Kozhanov
A. V. Cherkasov
V. K. Cherkasov
机构：
[1] Russian Academy of Sciences,G. A. Razuvaev Institute of Organometallic Chemistry
来源：
Russian Chemical Bulletin | 2017年 / 66卷
关键词：
sterically hindered 2,2,6,6-tetramethylpiperidine-1-oxyl; synthesis; one-electron reduction; heterospin biradicals; generation;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A nucleophilic addition reaction of 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (OH-TEMPO) to 3,6-di-tert-butyl-o-benzoquinone was used to obtain a new sterically hindered o-benzoquinone (1) containing 2,2,6,6-tetramethylpiperidineoxyl functional group, which was characterized by IR spectroscopy, mass spectrometry, elemental analysis, and X-ray diffraction. A one-electron reduction of 1 with potassium and thallium is an efficient method for the generation of earlier unknown heterospin biradicals 5a and 5b, respectively, containing nitroxide and o-semiquinone radical centers. Analysis of the hyperfine structure of the ESR spectra of biradicals 5a and 5b in solution showed that they belong to the group of heterospin biradicals with strong (J >> a) and fast exchange interaction between the radical centers.
引用
收藏
页码：1629 / 1635
页数：6
相关论文
共 50 条
  • [1] Heterospin biradicals based on new piperidineoxyl-substituted 3,6-di-tert-butyl-o-benzoquinone
    Egorova, E. N.
    Druzhkov, N. O.
    Kozhanov, K. A.
    Cherkasov, A. V.
    Cherkasov, V. K.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (09) : 1629 - 1635
  • [2] Photooxygenolysis of 3,6-di-tert-butyl-o-benzoquinone
    V. B. Vol’eva
    I. S. Belostotskaya
    N. L. Komissarova
    Z. A. Starikova
    L. N. Kurkovskaya
    Russian Journal of Organic Chemistry, 2006, 42 : 227 - 229
  • [3] Photooxygenolysis of 3,6-di-tert-butyl-o-benzoquinone
    Vol'eva, VB
    Belostotskaya, IS
    Komissarova, NL
    Starikova, ZA
    Kurkovskaya, LN
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (02) : 227 - 229
  • [4] Tin oxidation with 3,6-di-tert-butyl-o-benzoquinone
    A. V. Lado
    A. V. Piskunov
    O. V. Kuznetsova
    M. I. Timoshenkov
    M. S. Piskunova
    S. V. Maslennikov
    Russian Journal of Coordination Chemistry, 2008, 34 : 329 - 333
  • [5] The interaction of nickelocene with 3,6-di-tert-butyl-o-benzoquinone
    Piskunov, AV
    Fukin, GK
    Kurskii, YA
    Cherkasov, VK
    Abakumov, GA
    INORGANIC CHEMISTRY COMMUNICATIONS, 2005, 8 (04) : 339 - 342
  • [6] Tin oxidation with 3,6-di-tert-butyl-o-benzoquinone
    Lado, A. V.
    Piskunov, A. V.
    Kuznetsova, O. V.
    Timoshenkov, M. I.
    Piskunova, M. S.
    Maslennikov, S. V.
    RUSSIAN JOURNAL OF COORDINATION CHEMISTRY, 2008, 34 (05) : 329 - 333
  • [7] Zinc and cadmium complexes based on 3,6-di-tert-butyl-o-benzoquinone
    Piskunov, A. V.
    Maleeva, A. V.
    Abakumov, G. A.
    Cherkasov, V. K.
    Fukin, G. K.
    Bogomyakov, A. S.
    RUSSIAN JOURNAL OF COORDINATION CHEMISTRY, 2011, 37 (04) : 243 - 256
  • [8] Zinc and cadmium complexes based on 3,6-di-tert-butyl-o-benzoquinone
    A. V. Piskunov
    A. V. Maleeva
    G. A. Abakumov
    V. K. Cherkasov
    G. K. Fukin
    A. S. Bogomyakov
    Russian Journal of Coordination Chemistry, 2011, 37 : 243 - 256
  • [9] REDUCTION OF 3,6-DI-TERT-BUTYL-O-BENZOQUINONE BY HYDROGEN-CHLORIDE
    BELOSTOTSKAYA, IS
    VOLEVA, VB
    KOMISSAROVA, NL
    ERSHOV, VV
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1976, 25 (03): : 701 - 701
  • [10] EPR STUDY OF PHOTOREDUCTION OF ADDUCTS OF 3,6-DI-TERT-BUTYL-O-BENZOQUINONE WITH DICHLOROCARBENE
    PROKOFEV, AI
    MASALIMOV, AS
    VOLEVA, VB
    PROKOFEVA, TI
    BUBNOV, NN
    SOLODOVNIKOV, SP
    KABACHNIK, MI
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (04): : 738 - 743
12345