Electrochemical Oxidative Carbon-Atom Difunctionalization: Towards Multisubstituted Imino Sulfide Ethers was written by Guan, Zhipeng;Zhu, Shuxiang;Wang, Siyuan;Wang, Huamin;Wang, Siyuan;Zhong, Xingxing;Bu, Faxiang;Cong, Hengjiang;Lei, Aiwen. And the article was included in Angewandte Chemie, International Edition in 2021.COA of Formula: C10H22O The following contents are mentioned in the article:
Ethers (C-O/S) are ubiquitously found in a wide array of functional mols. and natural products. Nonetheless, the synthesis of imino sulfide ethers, containing an N(sp2)=C(sp2)-O/S fragment, still remains a challenge because of its sensitivity to acid. Developed here in is an unprecedented electrochem. oxidative carbon-atom difunctionalization of isocyanides, providing a series of novel multisubstituted imino sulfide ethers. Under metal-free and external oxidant-free conditions, isocyanides react smoothly with simple and readily available mercaptans and alcs. [e.g., 4-fluorobenzenethiol + Et isocyanoacetate + methanol → (Z)-I (80% isolated)]. Importantly, the procedure exhibited high stereoselectivities, excellent functional-group tolerance, and good efficiency on large-scale synthesis, as well as further derivatization of the products. This study involved multiple reactions and reactants, such as 3,7-Dimethyloctan-1-ol (cas: 106-21-8COA of Formula: C10H22O).
3,7-Dimethyloctan-1-ol (cas: 106-21-8) 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. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.COA of Formula: C10H22O
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts