Reductive Activation of Arenes. Part 21. Reaction of Products of Two-Electron Reduction of Arenecarbonitriles by Alkali Metals in Liquid Ammonia with Bromo- and Dibromoalkanes.

ChemInform ◽  
2007 ◽  
Vol 38 (15) ◽  
Author(s):  
T. A. Vaganova ◽  
E. V. Panteleeva ◽  
P. S. Yuferov ◽  
Yu. V. Rebitva ◽  
V. D. Shteingarts
Keyword(s):  
Alkali Metals ◽  
Liquid Ammonia ◽  
Reductive Activation ◽  
Electron Reduction

Reductive activation of arenes. VII. Alkylation of 9-cyanoanthracene two-electron reduction products in liquid ammonia.

Tetrahedron ◽  
1994 ◽  
Vol 50 (33) ◽  
pp. 10011-10020 ◽  
Author(s):  
Tamara A. Vaganova ◽  
Elena V. Panteleeva ◽  
Andrej P. Tananakin ◽  
Vitalij D. Shteingarts ◽  
Itzhak I. Bilkis
Keyword(s):  
Liquid Ammonia ◽  
Reductive Activation ◽  
Electron Reduction

ChemInform Abstract: Reductive Activation of Arenes. Part 7. Alkylation of 9- Cyanoanthracene Two-Electron Reduction Products in Liquid Ammonia.

ChemInform ◽  
2010 ◽  
Vol 26 (3) ◽  
pp. no-no
Author(s):  
T. A. VAGANOVA ◽  
E. V. PANTELEEVA ◽  
A. P. TANANAKIN ◽  
V. D. SHTEINGARTS ◽  
I. I. BILKIS
Keyword(s):  
Liquid Ammonia ◽  
Reductive Activation ◽  
Electron Reduction

Room Temperature Alkali Metal Reduction of Carbon Dioxide

2020 ◽  
Author(s):  
Lucas A. Freeman ◽  
Akachukwu D. Obi ◽  
Haleigh R. Machost ◽  
Andrew Molino ◽  
Asa W. Nichols ◽  
...  
Keyword(s):  
Alkali Metal ◽  
Alkali Metals ◽  
Room Temperature ◽  
Chemical Reduction ◽  
Bond Cleavage ◽  
Open Shell ◽  
Metal Reduction ◽  
One Pot ◽  
Earth Abundant ◽  
Electron Reduction

The reduction of the relatively inert carbon–oxygen bonds of CO<sub>2</sub> to access useful CO<sub>2</sub>-derived organic products is one of the most important fundamental challenges in synthetic chemistry. Facilitating this bond-cleavage using earth-abundant, non-toxic main group elements (MGEs) is especially arduous because of the difficulty in achieving strong inner-sphere interactions between CO<sub>2</sub> and the MGE. Herein we report the first successful chemical reduction of CO<sub>2</sub> at room temperature by alkali metals, promoted by a cyclic(alkyl)(amino) carbene (CAAC). One-electron reduction of CAAC-CO<sub>2</sub> adduct (<b>1</b>) with lithium, sodium or potassium metal yields stable monoanionic radicals clusters [M(CAAC–CO<sub>2</sub>)]<sub>n</sub>(M = Li, Na, K, <b> 2</b>-<b>4</b>) and two-electron alkali metal reduction affords open-shell, dianionic clusters of the general formula [M<sub>2</sub>(CAAC–CO<sub>2</sub>)]<sub>n </sub>(<b>5</b>-<b>8</b>). It is notable that these crystalline clusters of reduced CO<sub>2</sub> may also be isolated via the “one-pot” reaction of free CO<sub>2</sub> with free CAAC followed by the addition of alkali metals – a reductive process which does not occur in the absence of carbene. Each of the products <b>2</b>-<b>8</b> were investigated using a combination of experimental and theoretical methods.<br>

Reactions of aliphatic halides with solutions of alkali metals in liquid ammonia: I. Experiments with alkyl halides

2010 ◽  
Vol 81 (12) ◽  
pp. 1033-1052 ◽  
Author(s):  
A. Beverloo ◽  
M. C. Dieleman ◽  
P. E. Verkade ◽  
K. S. de Vries ◽  
B. M. Wepster
Keyword(s):  
Alkali Metals ◽  
Liquid Ammonia ◽  
Alkyl Halides

Steric Course of the Reduction of Ketoacetal Esters with Alkali Metals in Liquid Ammonia

1979 ◽  
Vol 18 (8) ◽  
pp. 637-638 ◽  
Author(s):  
Fritz Jaisli ◽  
Daniel Sternbach ◽  
Albert Eschenmoser ◽  
Masayuki Shibuya
Keyword(s):  
Alkali Metals ◽  
Liquid Ammonia

scholarly journals Enzymatic single-electron reduction and aerobic cytotoxicity of tirapazamine and its 1-oxide and nor-oxide metabolites

Chemija ◽  
2018 ◽  
Vol 29 (4) ◽  
Author(s):  
Jonas Šarlauskas ◽  
Aušra Nemeikaitė-Čėnienė ◽  
Audronė Marozienė ◽  
Lina Misevičienė ◽  
Mindaugas Lesanavičius ◽  
...  
Keyword(s):  
Side Effects ◽  
Anticancer Agent ◽  
Redox Cycling ◽  
Nitroaromatic Compounds ◽  
Single Electron ◽  
Reductive Activation ◽  
Cell Nuclei ◽  
Electron Reduction ◽  
Phenylene Diamine

Aerobic cytotoxicity of 3-amino-1,2,4-benzotriazine-1,4-dioxide (tirapazamine, TPZ), a bioreductively activated hypoxia-specific anticancer agent, is responsible for TPZ side effects in chemotherapy. In order to clarify its mechanisms, we examined the aerobic cytotoxicity of TPZ and its main metabolites, 3-amino-1,2,4-benzotriazine-1-oxide and 3-amino-1,2,4-benzotriazine in murine hepatoma MH22a cells, and their reduction by NADPH:cytochrome P-450 reductase (P-450R) and ferredoxin:NADP+ reductase (FNR). Analogous studies of several quinones and nitroaromatic compounds with similar values of single-electron reduction midpoint potentials (E17) were carried out. In single-electron reduction by P-450R and FNR, the reactivity of TPZ and its monoxide was similar to that of quinones and nitroaromatics, and increased with an increase in their E17. The cytotoxicity of TPZ and its metabolites possessed a prooxidant character, because it was partly prevented by an antioxidant N,N’-diphenyl-p-phenylene diamine and desferrioxamine, and potentiated by 1,3-bis(2-chloroethyl)-1-nitrosourea. Importantly, the cytotoxicity of TPZ and, possibly, its 1-N-oxide, was much higher than that of quinones and nitroaromatics with similar values of E17 and redox cycling activities. A possible additional factor in the aerobic cytotoxicity of TPZ is its reductive activation in oxygen-poor cell nuclei, leading to the formation of DNA-damaging species similar to those forming under hypoxia.

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