Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO2: Facile Synthesis of Diacids and Derivatization into Polyesters was written by Liao, Li-Li;Wang, Zhe-Hao;Cao, Ke-Gong;Sun, Guo-Quan;Zhang, Wei;Ran, Chuan-Kun;Li, Yiwen;Chen, Li;Cao, Guang-Mei;Yu, Da-Gang. And the article was included in Journal of the American Chemical Society in 2022.Recommanded Product: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:
A novel electrochem. ring-opening dicarboxylation of C-C single bonds in strained rings with CO2 was reported. Structurally diverse glutaric acid and adipic acid derivatives HO(O)CC(Ar1)R(CH2)nCH(Ar2)C(O)OH (R = H, Me, Ph; Ar1 = Ph, 3-methylphenyl, 2,3-dihydro-1-benzofuran-6-yl, etc.; n = 1, 2; Ar2 = Ph, 4-fluorohenyl, 3-methylphenyl) and HO(O)CC(R1)(R2)CH2CH(C(O)OR3)C(O)OH [R1 = H, Me, Ph; R2 = 4-tert-butylphenyl, C(O)OEt, 4-chlorophenyl, etc.; R3 = Et, (2S,5S)-5-methyl-2-(propan-2-yl)cyclohexyl, Ph, etc.] are synthesized from substituted cyclopropanes I, II and cyclobutanes III in moderate-to-high yields. In contrast to oxidative ring openings, it is also the first time to realize electro-reductive ring-opening reaction of strained rings, including commercialized ones. Control experiments suggest that radical anions and carbanions might be the key intermediates in this reaction. Moreover, this process features high step and atom economy, mild reaction conditions (1 atm, room temperature), good chemoselectivity and functional group tolerance, low electrolyte concentration, and easy derivatization of products. Furthermore, the polymerization of the corresponding diesters with diols is conducted to obtain a potential UV-shielding material with self-healing function and a fluorine-containing polyester, whose performance tests show a promising application. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Recommanded Product: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol).
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Recommanded Product: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts