5468-00-8Relevant academic research and scientific papers
Catalysis of Pd(II)-catalyzed acetalization of alkenes with diols
Hosokawa,Ataka,Murahashi
, p. 166 - 169 (1990)
Alkenes bearing electron-withdrawing substituents are catalytically acetalized with 1,3-propanediol only by the use of PdCl2(MeCN)2 catalyst under O2 atmosphere. When a combination of BiCl3 and LiCl is used as co-catalyst, the acetalization proceeds effectively. These results indicate that a hydroperoxopalladium(II) species is most likely an active catalyst in the present reaction.
Aromatic Monomers by in Situ Conversion of Reactive Intermediates in the Acid-Catalyzed Depolymerization of Lignin
Deuss, Peter J.,Scott, Martin,Tran, Fanny,Westwood, Nicholas J.,De Vries, Johannes G.,Barta, Katalin
supporting information, p. 7456 - 7467 (2015/06/30)
Conversion of lignin into well-defined aromatic chemicals is a highly attractive goal but is often hampered by recondensation of the formed fragments, especially in acidolysis. Here, we describe new strategies that markedly suppress such undesired pathways to result in diverse aromatic compounds previously not systematically targeted from lignin. Model studies established that a catalytic amount of triflic acid is very effective in cleaving the β-O-4 linkage, most abundant in lignin. An aldehyde product was identified as the main cause of side reactions under cleavage conditions. Capturing this unstable compound by reaction with diols and by in situ catalytic hydrogenation or decarbonylation lead to three distinct groups of aromatic compounds in high yields acetals, ethanol and ethyl aromatics, and methyl aromatics. Notably, the same product groups were obtained when these approaches were successfully extended to lignin. In addition, the formation of higher molecular weight side products was markedly suppressed, indicating that the aldehyde intermediates play a significant role in these processes. The described strategy has the potential to be generally applicable for the production of interesting aromatic compounds from lignin.
Photoinduced Molecular Transformations. Part 113. One-step Transformations of Cyclic Ethers into ω-Iodoalkyl Formates and of Aldehyde Cyclic Acetals into Monoesters of α,ω-Alkanediols by Iodoxyl Radical
Suginome, Hiroshi,Wang, Jian Bo
, p. 2825 - 2829 (2007/10/02)
The reaction of cyclic ethers with iodoxyl radical and iodine oxide gives the corresponding ω-iodoalkyl formates in one step; tetrahydrofuran can be transformed into ω-iodoalkyl formate in 31percent yield.Aldehyde cyclic acetals under conditions similar to the reaction of cyclic ethers lead to monoesters of α,ω-alkanediols in one step; cyclohexanecarboxaldehyde ethylene acetal gives 2-hydroxy cyclohexanecarboxylate in 60percent yield.The pathways leading to ω-iodoalkyl formatesand monoesters of α,ω-alkanediols are discussed based on the results of 18O-labelling studies with (18)OI and I2(18)O.
