《Stable, yet “”naked””, azo radical anion ArNNAr- and dianion ArNNAr2- (Ar = 4-CN-2,6-iPr2-C6H2) with selective CO2 activation》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Wang, Wenqing; Tan, Gengwen; Feng, Rui; Fang, Yong; Chen, Chao; Ruan, Huapeng; Zhao, Yue; Wang, Xinping. Synthetic Route of C10H20O5 The article mentions the following:
Azo radical anion (1-̇) and dianion 12- were isolated by 1- and two-electron reduction of the azo compound 1 (ArNNAr, Ar = 4-CN-2,6-iPr2-C6H2) with alkali metals, resp. The reduced species were characterized by single-crystal x-ray anal., EPR, UV and FTIR spectroscopy, as well as SQUID measurements. The filling of one and two electrons in the π* orbital of the N-N double bond of 1 leads to a half-double N-N bond in 1-̇ and a single N-N bond in 12-. The uncoordinated nature of these reduced species enables them to activate CO2. The exposure of 1 ̇- solution to CO2 gave oxalate anion C2O42-, while that of 12- solution to CO2 afforded the hydrazine dicarboxylate dianion [1-2CO2]2-, which is reversibly dissociated back to 1 and CO2 upon oxidation In the experiment, the researchers used many compounds, for example, 1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5Synthetic Route of C10H20O5)
1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5) is a member of crown ether Ligands. Crown-ethers are macrocyclic polyethers capable of forming host-guest complexes, especially with inorganic and organic cations. Crown-ethers can incorporate protonated primary amine compounds by formation of ion-dipole bonds with the oxygen atoms of the chiral selector. Crown-ethers have been widely used for the separation of several pharmaceuticals both in aqueous and non-aqueous media. Synthetic Route of C10H20O5
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem