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

来源：

MENDELEEV COMMUNICATIONS | 2021年 / 31卷 / 02期

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

页码：268 / 270

页数：3

共 50 条

[41] H•••O hydrogen bonding interactions for sterically hindered phenols and their phenoxyl radicals
Wang, Jinhu
Liu, Chunli
Liu, Xuejing
Shao, Linjun
Zhang, Xian-Man
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2019, 32 (05)
[42] Synthesis of Heavy Fluorous Ruthenium Metathesis Catalysts Using the Stereoselective Addition of Polyfluoroalkyllithium to Sterically Hindered Diimines
Hosek, Jan
Rybackova, Marketa
Cejka, Jan
Cvacka, Josef
Kvicala, Jaroslav
ORGANOMETALLICS, 2015, 34 (13) : 3327 - 3334
[43] New Sterically Hindered Bis-o-Benzoquinones with Electron-Donor Bridging Groups and Related Binuclear Triphenylantimony(V) Catecholate Complexes
Bukhvalova, S. Yu
Zhiganshina, E. R.
Astaf'eva, T., V
Arsenyev, M., V
Baranov, E., V
Chesnokov, S. A.
Poddel'sky, A., I
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY, 2020, 46 (12) : 817 - 827
[44] Novel synthesis of sterically hindered N-substituted lactams from imides
Sannigrahi, Mousumi
Pinto, Patrick
Chan, T. M.
Shih, Neng-Yang
Njoroge, F. George
TETRAHEDRON LETTERS, 2006, 47 (28) : 4877 - 4880
[45] Synthesis and study of electrochemical properties of the sterically hindered phenol derivatives and the corresponding radicals
Khubaeva, T. O.
Zakaeva, R. Sh.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2012, 82 (03) : 446 - 454
[46] Synthesis and study of electrochemical properties of the sterically hindered phenol derivatives and the corresponding radicals
T. O. Khubaeva
R. Sh. Zakaeva
Russian Journal of General Chemistry, 2012, 82 : 446 - 454
[47] Alkylation of catechol with cyclohexene. Novel sterically hindered o-quinones and catechols
Kocherova, T. N.
Druzhkov, N. O.
Martyanov, K. A.
Shavyrin, A. S.
Arsenyev, M., V
Kulikova, T., I
Baranov, E., V
Kuropatov, V. A.
Cherkasov, V. K.
RUSSIAN CHEMICAL BULLETIN, 2020, 69 (12) : 2383 - 2389
[48] Multinuclear compounds of s-elements with sterically hindered o-semiquinonates and catecholates
Fokin, S. V.
Letyagin, G. A.
Romanenko, G. V.
Bogomyakov, A. S.
Petrova, M. V.
Morozov, V. A.
Ovcharenko, V. I.
RUSSIAN CHEMICAL BULLETIN, 2018, 67 (01) : 61 - 70
[49] Study of the mechanism of redox transformations of sterically hindered N-aryl-o-iminoquinones
Smolyaninov, I. V.
Letichevskaya, N. N.
Kulakov, A. V.
Aref'ev, Ya. B.
Pashchenko, K. P.
Berberova, N. T.
RUSSIAN JOURNAL OF ELECTROCHEMISTRY, 2007, 43 (10) : 1187 - 1199
[50] Study of the mechanism of redox transformations of sterically hindered N-aryl-o-iminoquinones
I. V. Smolyaninov
N. N. Letichevskaya
A. V. Kulakov
Ya. B. Aref’ev
K. P. Pashchenko
N. T. Berberova
Russian Journal of Electrochemistry, 2007, 43 : 1187 - 1199

← 1 2 3 4 5 →