141-27-5Relevant academic research and scientific papers
Oxidation by Chemical Manganese Dioxide. Part 3.1 Oxidation of Benzylic and Allylic Alcohols, Hydroxyarenes and Aminoarenes
Hirano, Masao,Yakabe, Sigetaka,Chikamori, Hideki,Clark, James H.,Morimoto, Takashi
, p. 770 - 771 (1998)
The combined use of chemical manganese dioxide (CMD) and molecular sieves in hexane (or in acetone) in general or CMD alone in particular cases enables the convenient and efficient oxidation of benzylic and allylic alcohols, phenols and amines under relatively mild conditions.
Total Synthesis of (-)-Phorbaketal A
Joung, Seewon,Kim, Rira,Lee, Hee-Yoon
, p. 3903 - 3906 (2017)
A convergent asymmetric total synthesis of phorbaketal A was achieved in 10 steps through a Au(I)-catalyzed intramolecular spiroketalization reaction of an alkyne diol intermediate prepared from (R)-carvone and geranial. The spiroketalization reaction was
3,5-dimethylpyrazolium fluorochromate(VI)-catalysed oxidation of organic substrates by hydrogen peroxide under solvent-free conditions
Chaudhuri, Mihir K.,Dehury, Sanjay K.,Hussain, Sahid,Duarah, Ankur,Gogoi, Nayanmoni,Lakshmi Kantam
, p. 1349 - 1352 (2005)
3,5-Dimethylpyrazolium fluorochromate (VI), C5H 8N2H[CrO3F], DmpzHFC, serves as an efficient catalyst for oxidation of primary, secondary and allylic alcohols to the corresponding carbonyl compounds using H2O2 at room temperature under solvent-free conditions. Oxidation of methyl phenyl sulfides and triphenylphosphine were also carried out successfully.
Transition Metal-Substituted Potassium Silicotungstate Salts as Catalysts for Oxidation of Terpene Alcohols with Hydrogen Peroxide
da Silva, Marcio Jose,da Silva Andrade, Pedro Henrique,Sampaio, Vinicius Fernando Coelho
, p. 2094 - 2106 (2021)
Abstract: In this work, the catalytic activity of the transition metal-substituted potassium silicotungstate salts (i.e. K8-nSiMn+W11O39 (Mn+ = Cu2+, Co2+, Ni2+, Zn2+ and Fe3+) was investigated on the oxidation reactions of the terpene alcohols with H2O2 aqueous solution. The metal-substituted silicotungstate salts were easily synthesized in one-pot reactions of the precursor metal solutions (i.e. Na2WO4, Na2SiO3 and MCln) with KCl added in stoichiometric amount; after this precipitation step, the solid heteropoly salts were filtered and dried in an oven. This procedure of synthesis avoids multi-step processes that starts from the pristine heteropolyacid. The substituted metal heteropoly salts were characterized by infrared spectroscopy, measurements of the specific surface area (BET) and porosimetry by isotherms of adsorption/desorption of N2, X-rays diffraction, thermal analyses, dispersive X-rays spectroscopy, scanning electronic microscopy. The acidity strength was estimated by potentiometric titration with n-butylamine. All the salts were evaluated as catalysts in terpenic alcohols oxidation reactions with H2O2. The K5SiFeW11O39 was the most active and selective catalyst toward oxidation products. The impacts of the main reaction variables such as catalyst concentration, temperature, oxidant load, and nature of the terpene substrate were assessed. The highest activity of the K5SiFeW11O39 catalyst was assigned to the highest Lewis acidity. Graphic Abstract: [Figure not available: see fulltext.].
Asymmetric total synthesis of ieodomycin B
Lin, Shuangjie,Zhang, Jianting,Zhang, Zhibin,Xu, Tianxiang,Huang, Shuangping,Wang, Xiaoji
, (2017)
Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection-lactonization one-pot reaction.
Remarkable substituent effects on the oxidizing ability of triarylbismuth dichlorides in alcohol oxidation
Matano, Yoshihiro,Hisanaga, Teppei,Yamada, Hisatsugu,Kusakabe, Shingo,Nomura, Hazumi,Imahori, Hiroshi
, p. 8676 - 8680 (2004)
Substituent effects on the oxidizing ability of triarylbismuth dichlorides were examined by intermolecular and intramolecular competition experiments on geraniol oxidation in the presence of DBU. It was found that the oxidizing ability of the dichlorides increases with increasing electron-withdrawing ability of the para substituents, and by introduction of a methyl group at the ortho position of the aryl ligands attached to the bismuth. The intermolecular and intramolecular H/D kinetic isotope effects observed for the competitive oxidation of p-bromobenzyl alcohols indicate that the rate-determining step involves C-H bond cleavage. Several primary and secondary alcohols were oxidized efficiently under mild conditions by the combined use of newly developed organobismuth(V) oxidants and DBU.
Highly efficient aerobic oxidation of benzylic and allylic alcohols by a simple catalyst system of [RuCl2(p-cymene)]2/Cs2CO3
Lee,Chang
, p. 7507 - 7510 (2000)
A new catalyst system of [RuCl2(p-cymene)]2/Cs2CO3 has been disclosed for highly efficient aerobic oxidation of activated alcohols to the corresponding carbonyl compounds, which is characterized by its high selectivity and activity, operational simplicity, and low air and moisture sensitivity. (C) 2000 Elsevier Science Ltd.
POLYMER-ANCHORED VANADIUM(V) AND MOLYBDENUM(VI) CATALYSTS FOR THE REGIOSELECTIVE EPOXIDATION OF (E)-GERANIOL WITH t-BUTYL HYDROPEROXIDE
Yokoyama, Toshiro,Nishizawa, Masato,Kimura, Tetsuo,Suzuki, Toshishige M.
, p. 1703 - 1706 (1983)
The reaction of (E)-geraniol with t-BuOOH in the presence of polymer-anchored VV or MoVI complexes gave 2,3-epoxygeraniol in high yields.The conversion and the selectivity by the MR-type polymer catalysts containing VV were comparable to those given by homogeneous catalyst based on VO(acac)2.The present catalysts can be used repeatedly without causing significant decrease in catalytic activity.
Pt-Catalyzed selective oxidation of alcohols to aldehydes with hydrogen peroxide using continuous flow reactors
Kon, Yoshihiro,Nakashima, Takuya,Yada, Akira,Fujitani, Tadahiro,Onozawa, Shun-Ya,Kobayashi, Shū,Sato, Kazuhiko
supporting information, p. 1115 - 1121 (2021/02/16)
The oxidation of alcohols to aldehydes is a powerful reaction pathway for obtaining valuable fine chemicals used in pharmaceuticals and biologically active compounds. Although many oxidants can oxidize alcohols, only a few hydrogen peroxide oxidations can be employed to continuously synthesize aldehydes in high yields using a liquid-liquid two-phase flow reactor, despite the possibility of the application toward a safe and rapid multi-step synthesis. We herein report the continuous flow synthesis of (E)-cinnamaldehyde from (E)-cinnamyl alcohol in 95%-98% yields with 99% selectivity for over 5 days by the selective oxidation of hydrogen peroxide using a catalyst column in which Pt is dispersed in SiO2. The active species for the developed selective oxidation is found to be zero-valent Pt(0) from the X-ray photoelectron spectroscopy measurements of the Pt surface before and after the oxidation. Using Pt black diluted with SiO2as a catalyst to retain the Pt(0) species with the optimal substrate and H2O2introduction rate not only enhances the catalytic activity but also maintains the activity during the flow reaction. Optimizing the contact time of the substrate with Pt and H2O2using a flow reactor is important to proceed with the selective oxidation to prevent the catalytic H2O2decomposition.
An alkenate compound containing an aromatic ring and its preparation and application
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Paragraph 0049-0052, (2022/01/04)
The present invention discloses an enoate compound containing an aromatic ring and its preparation and application. The compound structure of the present invention is simple, easy to synthesize, synthetic raw materials are derived from natural products, pollution-free to the environment, eco-friendly. The compounds provided by the present invention have a good repellent and killing effect on aphids, while having a good inhibitory activity against plant pathogens, can be used as an aphid control agent and fungicide, and have good application prospects in the green prevention and control of pests and plant diseases.
