scholarly journals Reaction of 2,5-dihydroxy-[1,4]-benzoquinone with nucleophiles – ipso-substitution vs. addition/elimination

2020 ◽  
Vol 56 (84) ◽  
pp. 12845-12848
Author(s):  
Hubert Hettegger ◽  
Karin Steinkellner ◽  
Nele S. Zwirchmayr ◽  
Antje Potthast ◽  
Kevin J. Edgar ◽  
...  

ipso-Substitution vs. addition/elimination reaction depending on the type of nucleophile reacting with 2,5-dihydroxy-[1,4]-benzoquinone (DHBQ).


1978 ◽  
Vol 9 (24) ◽  
Author(s):  
L. TESTAFERRI ◽  
M. TIECCO ◽  
M. TINGOLI ◽  
M. FIORENTINO ◽  
L. TROISI


1973 ◽  
Vol 248 (6) ◽  
pp. 1946-1955 ◽  
Author(s):  
Christopher T. Walsh ◽  
Elizabeth Krodel ◽  
Vincent Massey ◽  
Robert H. Abeles




Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4446
Author(s):  
Giancarlo V. Botteselle ◽  
Welman C. Elias ◽  
Luana Bettanin ◽  
Rômulo F. S. Canto ◽  
Drielly N. O. Salin ◽  
...  

Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium.



1969 ◽  
Vol 22 (7) ◽  
pp. 1405 ◽  
Author(s):  
JJ Brophy ◽  
MJ Gallagher

Cyclic and acyclic bis-phosphonium salts with a two-carbon bridge are smoothly cleaved to phosphines in high yield by potassium cyanide in dimethyl sulphoxide. Evidence is presented that the reaction proceeds by an elimination-addition sequence. An elimination reaction also occurs when sodium methoxide, sodium azide, sodium acetate, and triethylamine react with ethane-1,2-bis(tri-phenylphosphonium) dibromide. ��� In a novel reaction, triphenylphosphine is converted into its oxide by a mixture of sodium azide and dimethyl sulphoxide.



ChemInform ◽  
2010 ◽  
Vol 29 (44) ◽  
pp. no-no
Author(s):  
S. A. GIACOBBE ◽  
D. BARALDI ◽  
R. DI FABIO


2005 ◽  
Vol 732 (1-3) ◽  
pp. 55-61 ◽  
Author(s):  
Jesús M. Ruiz Gonzalez ◽  
Marcos Loroño ◽  
Tania Córdova ◽  
Gabriel Chuchani


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