Anionic products of the two-electron reduction of aromatic nitriles in liquid ammonia

1994 ◽  
Vol 7 (3) ◽  
pp. 153-161 ◽  
Author(s):  
Isaak I. Bilkis ◽  
Tamara A. Vaganova ◽  
Elena V. Panteleeva ◽  
Georgij E. Salnikov ◽  
Andrej P. Tananakin ◽  
...  
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

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

1976 ◽  
Vol 73 ◽  
pp. 849-851 ◽  
Author(s):  
Thomas Kottarathil ◽  
Gérard Lepoutre

2020 ◽  
Author(s):  
Lucas A. Freeman ◽  
Akachukwu D. Obi ◽  
Haleigh R. Machost ◽  
Andrew Molino ◽  
Asa W. Nichols ◽  
...  

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>


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