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
  • [21] Electronic Structure and Magnetic Properties of o-Benzoquinone Iron Complexes with Tetraazamacrocyclic Ligands
    A. A. Starikova
    E. A. Metelitsa
    A. G. Starikov
    Journal of Structural Chemistry, 2019, 60 : 1219 - 1225
  • [22] The Synthesis of Sterically Hindered Amides
    Schaefer, Gabriel
    Bode, Jeffrey W.
    CHIMIA, 2014, 68 (04) : 252 - 255
  • [23] Synthesis of sterically hindered porphyrins
    Parpia, MO
    Reinert, TJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : U244 - U244
  • [24] SYNTHESIS OF STERICALLY HINDERED IMINES
    LOVE, BE
    REN, JH
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20): : 5556 - 5557
  • [25] Influence of o-benzoquinone nature on initiation of radical polymerization by the o-benzoquinone-tert-amine system
    Chesnokov, SA
    Cherkasov, VK
    Abakumov, GA
    Mamysheva, ON
    Chechet, YV
    Nevodchikov, VI
    RUSSIAN CHEMICAL BULLETIN, 2001, 50 (12) : 2366 - 2371
  • [26] New Tin(IV) Complexes with Sterically Hindered o-Iminobenzoquinone Ligand: Synthesis and Structure
    Piskunov, Alexandr V.
    Mescheryakova, Irina N.
    Fukin, Georgii K.
    Bogomyakov, Artyem S.
    Romanenko, Galina V.
    Cherkasov, Vladimir K.
    Abakumov, Gleb A.
    HETEROATOM CHEMISTRY, 2009, 20 (06) : 332 - 340
  • [27] PI-ELECTRONIC ENERGY LEVELS OF O-BENZOQUINONE
    KUBOYAMA, A
    WADA, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1965, 38 (10) : 1709 - +
  • [28] ESTERIFICATION OF STERICALLY HINDERED CARBOXYLIC ACIDS WITH TRIETHYLOXONIUM FLUOROBORATE
    RABER, DJ
    GARIANO, P
    TETRAHEDRON LETTERS, 1971, (49) : 4741 - &
  • [29] CYCLOADDITION OF 3-SUBSTITUTED INDOLES WITH O-BENZOQUINONE
    KOMATSU, T
    NISHIO, T
    OMOTE, Y
    CHEMISTRY & INDUSTRY, 1978, (03) : 95 - 95
  • [30] Synthesis, structure, and reactivity of some sterically hindered (silylamino)phosphines
    Samuel, RC
    Kashyap, RP
    Krawiec, M
    Watson, WH
    Neilson, RH
    INORGANIC CHEMISTRY, 2002, 41 (26) : 7113 - 7124