26831-63-0Relevant academic research and scientific papers
Synthesis and characterization of N-hydroxyphthalimide immobilized on SiO2-coated Fe3O4 nanoparticles as magnetic catalyst for oxidation of benzyl alcohols and hydrocarbons
Hosseinzadeh, Rahman,Mavvaji, Mohammad,Tajbakhsh, Mahmood,Lasemi, Zahra
, p. 893 - 904 (2018/03/01)
In this study, N-hydroxyphthalimide (NHPI) was successfully attached on functionalized SiO2-coated Fe3O4 nanoparticles through amid bond. The sustained nanomagnetite-immobilized NHPI as a new magnetically recoverable catalyst was characterized by FT-IR, XRD, TGA, VSM, TEM and SEM techniques. The prepared catalyst exhibited high selectivity for oxidation of various benzyl alcohols and hydrocarbons in the presence of hydrogen peroxide as oxidant. The catalyst can be readily separated from the reaction mixture using an external magnet and reused several times without significant loss of its catalytic activity.
Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose
Li, Guangyi,Li, Ning,Zheng, Mingyuan,Li, Shanshan,Wang, Aiqin,Cong, Yu,Wang, Xiaodong,Zhang, Tao
, p. 3607 - 3613 (2016/07/06)
A new route for the selective synthesis of renewable 1,3-cyclopentanediol was developed by the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone followed by hydrogenation. The presence of a small amount of base catalysts is beneficial for the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone. Such a promotion effect of base catalysts can be rationalized by restraining the generation of levulinic acid which may catalyze the polymerization of furfuryl alcohol. In the hydrogenation of 4-hydroxycyclopent-2-enone to 1,3-cyclopentanediol, an evident solvent effect was noticed. Higher carbon yields of 1,3-cyclopentanediol were obtained when tetrahydrofuran was used as the solvent. In the large scale tests with high initial concentrations of feedstocks, a high overall carbon yield (72.0%) of 1,3-cyclopentanediol was achieved over cheap catalysts (MgAl-HT and RANEY Ni). As a potential application, 1,3-cyclopentanediol as obtained was successfully used as a monomer in the synthesis of polyurethane.
PALLADIUM(0) CATALYZED REACTIONS OF 1,4-EPIPEROXIDES
Suzuki, Masaaki,Oda, Yoshihisa,Hamanaka, Nobuyuki,Noyori, Ryoji
, p. 517 - 535 (2007/10/02)
The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses.The Pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products.From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2;3,4-diepoxides, and 1,4-diols.The results are interpreted in terms of competing Pd(0)/Pd(II) exchange mechanisms.Exposure of prostaglandin (PG) H2 methyl esterto Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PGF2α, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.
Ruthenium(II)-Catalyzed Reactions of 1,4-Epiperoxides
Suzuki, Masaaki,Ohtake, Hiroaki,Kameya, Yoshimi,Hamanaka, Nobuyuki,Noyori, Ryoji
, p. 5292 - 5302 (2007/10/02)
The behavior of 1,4-epiperoxides in the presence of transition-metal complexes is highly dependent on the structures of the substrates and the nature of the metal catalysts.Reaction of saturated epiperoxides such as 1,3-epiperoxycyclopentane, 1,4-epiperoxycyclohexane, or dihydroascaridole catalyzed by RuCl2(PPh3)3 in dichloromethane gives a mixture of products arising from fragmentation, rearrangement, reduction, disproportionation, etc.Prostaglandin H2 methyl ester undergoes clean and stereospecific fragmentation to afford methyl(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoate and malonaldehyde.Bicyclic 2,3-didehydro 1,4-epiperoxides give the syn-1,2:3,4-diepoxides by the same catalyst.The monocyclic analogues are transformed to a mixture of diepoxides and furan products.The stereochemical outcome of the epoxide formation reflects unique differences in the ground-state geometry of the starting epiperoxide substrates.FeCl2(PPh3)2 serves as a useful catalyst for the skeletal change of sterically hindered bicyclic 2,3-didehydro 1,4-epiperoxides to the syn-diepoxides.In addition, the Fe complex best effects the conversion of 1,4-unsubstituted 2,3-didehydro epiperoxides to furans.The Ru-catalyzed reactions are interpreted in terms of the intermediacy of inner-sphere radicals formed by atom transfer of the Ru(II) species to peroxy substrates, in contrast to the Fe-catalyzed reactions proceeding via free, outer-sphere radicals generated by an electron-transfer mechanism.
Base-Catalyzed Fragmentation of 2,3-Dioxabicycloheptane, the Bicyclic Peroxide Nucleus of Prostaglandin Endoperoxides: Large Secondary Deuterium Kinetic Isotope Effects
Zagorski, Michael G.,Salomon, Robert G.
, p. 1750 - 1759 (2007/10/02)
The influence of deuterium substitution on the rates of base-catalyzed rearrangements of 2,3-dioxabicycloheptane (1) is examined.The kinetic isotope effect observed previously with 1,4,5,6,7,7-hexadeuterio-1 (kH/kD = 7-8) is much larger than that observed with 1-deuterio-1 (kH/kD = 3-4) during fragmentation to levulinaldehyde.This reveals a large cumulative secondary deuterium isotope effect which accompanies rate-determining cleavage of the bridgehead C-H bond.Presumably cleavage of the C4-C7 bond also occurs during the rate-determining step and deuterium substitution on these carbons produces large secondary kinetic isotope effects.
