Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water was written by Peng, Henian;Li, Tiejun;Tian, Duanshuai;Yang, He;Xu, Guangqing;Tang, Wenjun. And the article was included in Organic & Biomolecular Chemistry in 2021.HPLC of Formula: 605-94-7 This article mentions the following:
A series of unsaturated carbonyls, quinones and pyridinium salts were effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes and di- and tetrahydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient and metal-free reduction system. Deuterium-labeling experiments revealed this protocol to be an exclusive transfer hydrogenation process from water. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7HPLC of Formula: 605-94-7).
2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).HPLC of Formula: 605-94-7
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem