Synthesis and structure of sterically hindered o-benzoquinone carboxylic acid

被引:2
|
作者
Zherebtsov, Maxim A. [1 ,2 ]
Arsenyev, Maxim, V [1 ,2 ]
Baranov, Evgeny, V [1 ]
Chesnokov, Sergey A. [1 ]
Cherkasov, Vladimir K. [1 ,2 ]
机构
[1] Russian Acad Sci, GA Razuvaev Inst Organometall Chem, Nizhnii Novgorod 603950, Russia
[2] NI Lobachevsky State Univ Nizhny Novgorod, Nizhnii Novgorod 603950, Russia
基金
俄罗斯基础研究基金会;
关键词
catechol; pyrocatechuic acid; oxidation; X-ray; o-quinone; cyclic voltammetry; MACROCYCLIC CHELATOR; MECHANISM; CATECHOL; QUINONE; REDUCTION; COMPLEXES; OXIDATION; ROUTE; GUEST;
D O I
10.1016/j.mencom.2021.03.042
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2,4-Di-tert-butyl-5,6-dioxocyclohexa-1,3-diene-1-carboxylic acid, an oxidized analogue of sterically hindered pyrocatechuic acid, was obtained from 4,6-di-tert-butyl-2,3dihydroxybenzaldehyde in four stages. The electrochemical reduction of this compound proceeds in two stages: the first reduction wave (Ered1 = ?0.24 V) is irreversible, while the second stage is partially reversible (E1/2, red2 = ?0.65 V). The molecular structure of the o-quinone carboxylic acid in the crystalline state was comfirmed by single-crystal X-ray analysis.
引用
收藏
页码:268 / 270
页数:3
相关论文
共 50 条
  • [41] UNUSUAL SYNTHESIS, STRUCTURE, AND THERMOCHROMIC PROPERTIES OF NOVEL STERICALLY HINDERED CYCLOHEXADIENES
    KOMISSAROV, VN
    UKHIN, LY
    KHARLANOV, VA
    VETOSHKINA, LV
    KONSTANTINOVSKI, LE
    ALDOSHIN, SM
    FILIPENKO, OS
    NOVOZHILOVA, MA
    ATOVMYAN, LO
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1991, 40 (05): : 1003 - 1010
  • [42] SYNTHESIS AND PROPERTIES OF STERICALLY HINDERED OXYSTIRYLPYRIDINES
    BOGDANOV, GN
    ROZENBER.AN
    SHEINKMA.AK
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1971, (12): : 1660 - &
  • [43] Synthesis of a sterically hindered metallocene catalyst
    Clifford, Kaitlin M.
    Broene, Richard D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [44] Synthesis of sterically hindered cyclic amines
    Santhan-Oommen, Reuben
    Daugulis, Olafs
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [45] Synthesis, Structure of Phosphorylated Sterically Hindered Methylene Quinones and Ylides Thereof
    Galkina, I. V.
    Andriyashkin, V. V.
    Romanov, S. R.
    Abzhalelov, B. B.
    Kuzhamberdieva, S. Zh.
    Topalova, A. S.
    Litvinov, I. A.
    Bakhtiyarova, Yu. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (08) : 1084 - 1092
  • [46] SYNTHESIS OF STERICALLY HINDERED AROMATIC DIALDEHYDES
    YAKUBOV, AP
    TSYGANOV, DV
    BELENKII, LI
    KRAYUSHKIN, MM
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1991, 40 (07): : 1509 - 1512
  • [47] Synthesis of new sterically hindered anilines
    Steele, Barry R.
    Georgakopoulos, Spyros
    Micha-Screttas, Maria
    Screttas, Constantinos G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (19) : 3091 - 3094
  • [48] Valence tautomerism in a o-benzoquinone adduct of a tetraazamacrocycle complex of manganese
    Caneschi, A
    Dei, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (21) : 3005 - 3007
  • [49] Experimental and theoretical study of the electrochemical behavior of o-benzoquinone and pyrocatechol
    Song, Yuan-zhi
    SPECTROSCOPY LETTERS, 2007, 40 (06) : 811 - 833
  • [50] Synthesis, Structure of Phosphorylated Sterically Hindered Methylene Quinones and Ylides Thereof
    I. V. Galkina
    V. V. Andriyashkin
    S. R. Romanov
    B. B. Abzhalelov
    S. Zh. Kuzhamberdieva
    A. S. Topalova
    I. A. Litvinov
    Yu. V. Bakhtiyarova
    Russian Journal of Organic Chemistry, 2022, 58 : 1084 - 1092