Mild Heterogeneous Palladium-Catalyzed Cleavage of β-O-4′-Ether Linkages of Lignin Model Compounds and Native Lignin in Air was written by Galkin, Maxim V.;Sawadjoon, Supaporn;Rohde, Volker;Dawange, Monali;Samec, Joseph S. M.. And the article was included in ChemCatChem in 2014.Product Details of 3929-47-3 This article mentions the following:
A mild and robust heterogeneous palladium-catalyzed C-O bond cleavage of 2-aryloxy-1-arylethanols using formic acid as reducing agent in air was developed. The cleaved products were isolated in 92-98% yield; and by slightly varying the reaction conditions, a ketone, an alc., or an alkane can be generated in near-quant. yield. This reaction is applicable to cleaving the β-O-4′-ether bond found in lignin polymers of different origin. The reaction was performed on a lignin polymer model to generate either the monomeric aryl ketone or alkane in a quant. yield. Moderate depolymerization was achieved with native lignin at similar reaction conditions. Mechanistic studies under kinetic control indicate that an initial palladium-catalyzed dehydrogenation of the alc. is followed by insertion of palladium to an enol equivalent A palladium-formato complex reductively cleaves the palladium-enolate complex to generate the ketone. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Product Details of 3929-47-3).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Product Details of 3929-47-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem