1860-29-3

Upstream product

• 108-94-1 cyclohexanone 
• 67-63-0 isopropyl alcohol 
• 110-83-8 cyclohexene 
• 1146-49-2 <2-(p-tolylsulfonyl)hydrazino>cyclohexane 
• 74-98-6 propane 
• 108-93-0 cyclohexanol 
• 2741-16-4 isopropoxybenzene 
• 90-05-1 2-methoxy-phenol 

Relevant academic research and scientific papers

Polysilane-Immobilized Rh-Pt Bimetallic Nanoparticles as Powerful Arene Hydrogenation Catalysts: Synthesis, Reactions under Batch and Flow Conditions and Reaction Mechanism

Hydrogenation of arenes is an important reaction not only for hydrogen storage and transport but also for the synthesis of functional molecules such as pharmaceuticals and biologically active compounds. Here, we describe the development of heterogeneous Rh-Pt bimetallic nanoparticle catalysts for the hydrogenation of arenes with inexpensive polysilane as support. The catalysts could be used in both batch and continuous-flow systems with high performance under mild conditions and showed wide substrate generality. In the continuous-flow system, the product could be obtained by simply passing the substrate and 1 atm H2 through a column packed with the catalyst. Remarkably, much higher catalytic performance was observed in the flow system than in the batch system, and extremely strong durability under continuous-flow conditions was demonstrated (>50 days continuous run; turnover number >3.4 × 105). Furthermore, details of the reaction mechanisms and the origin of different kinetics in batch and flow were studied, and the obtained knowledge was applied to develop completely selective arene hydrogenation of compounds containing two aromatic rings toward the synthesis of an active pharmaceutical ingredient.

Catalytic transfer hydrogenation/hydrogenolysis of guaiacol to cyclohexane over bimetallic RuRe/C catalysts

The hydrodeoxygenation of lignin monomer guaiacol via catalytic transfer hydrogenation was studied with 2-propanol as a hydrogen donor and Ru-based catalysts. Guaiacol was mainly converted into a partially deoxygenated product, cyclohexanol (>?70% selectivity), over Ru/C catalysts with the hydrogen produced in-situ from 2-propanol. An addition of Re to Ru/C catalysts significantly enhanced the rate of C—O hydrogenolysis, resulting in the complete deoxygenation to cyclohexane (~?60% selectivity). The remarkable deoxygenation ability of the bimetallic RuRe/C catalyst is attributed to its bifunctional characteristic, by which Ru catalyzes the hydrogenation-hydrogenolysis of guaiacol and Re provides acid sites to promote cyclohexane production via hydrogenolysis.

Syntheses and conformational analyses of mono- and trans-1,4-dialkoxy substituted cyclohexanes-the steric substituent/skeleton interactions

Mono- and trans-1,4-dialkoxy substituted cyclohexanes (alkyl=Me, Et, i-Pr, t-Bu) were prepared using the solvomercuration-demercuration (SM-DM) procedure. The axial?axial and axial,axial?equatorial, equatorial conformational equilibria of the products wer

Catalytic reductive etherification of ketones with alcohols at ambient hydrogen pressure: A practical, waste-minimized synthesis of dialkyl ethers

A heterogeneous platinum catalyst was found to efficiently mediate the reductive etherification of ketones at ambient hydrogen pressure. In this environmentally benign transformation, water is released as the only by-product, and this is trapped with molecular sieves. The preparative utility of the new reaction protocol is demonstrated by the synthesis of ten unsymmetrical ethers from the corresponding ketones and primary or secondary alcohols. Georg Thieme Verlag Stuttgart.

Addition of Alcohol to Olefinic Bonds by Paired Electrosynthesis with Raney-Nickel Cathode

A one-pot addition reaction of an alcohol to an olefinic double bond was successfully performed by use of paired electrosynthesis with a Raney-nickel cathode.

Solvomercuration-Demercuration. 12. The Solvomercuration-Demercuration of Olefins in Alcohol Solvents with Mercuric Trifluoroacetate--An Ether Synthesis of Wide Generality

Studies on the solvomercuration-demercuration (SM-DM) of olefins in methyl, ethyl, isopropyl, and tert-butyl alcohols with mercuric trifluoroacetate have been extended. 1-Dodecene undergoes the SM-DM sequence with typical results for a monosubstituted olefin.Cyclopentene similarly exhibited behavior characteristic of a 1,2-disubstituted olefin in methanol, ethanol, and 2-propanol, giving high yields, >90percent of the corresponding ethers.However, in tert-butyl alcohol, the yields of ether were lower than normal and decreased somewhat with time. 2-Methyl-1-butene gives >90percent yields of the Markovnikov methyl ether.On the other hand, the yields of ethyl, isopropyl, and tert-butyl ethers are lower and decrease with time.Major improvements in yields, however, are possible by lowering the reaction temperature from room temperature to 0 deg C.Cyclooctene, surprisingly, behaves more like a tri-, tetra-, or isosubstituted olefin than a 1,2-disubstituted olefin.The yields of cyclooctyl methyl ether are >90percent and do not decrease with time.However, yields of the ethyl, isopropyl, and tert-butyl ethers are lower and drop with time.Again, lowering the reaction temperature from room temperature to 0 deg C markedly improves the yields of the cyclooctyl ethers.These results, coupled with those of a previous study, clearly reveal the exceptional superiority of mercuric trifluoroacetate for the SM-DM of olefins in alcohol solvents.

Solvomercuration-Demercuration. 11. Alkoxymercuration-Demercuration of Representative Alkenes in Alcohol Solvents with the Mercuric Salts Acetate, Trifluoroacetate, Nitrate, and Methanesulfonate

The alkoxymercuration-demercuration of seven representative olefins with the mercuric salts acetate, trifluoroacetate, nitrate, and methanesulfonate, in methyl, ethyl, isopropyl, and tert-butyl alcohols was examined.Mercuric acetate was effective only in methanol and ethanol.On the other hand, mercuric trifluoroacetate was effective in all four solvents, giving in most cases high yields of the corresponding ethers.Both mercuric nitrate and mercuric methanesulfonate were effective in methanol, ethanol, and 2-propanol.However, in several cases poor selectivity for the ether was observed, as evidenced by the formation of significant amounts of side products.Both electronic and steric effects are important factors in the reaction.Moreover, the structure of the olefin has a pronounced effect, both on the types of oxymercurials formed and on their stability to the reaction conditions.

OXIDATION OF N-ALKYL-N'-TOSYLHYDRAZINES WITH Hg(OAc)2. A NEW SYNTHESIS OF ETHERS

N-Alkyl-N'-tosylhydrazines with Hg(OAc)2 in the presence of alcohols or phenol give high yields of corresponding ethers.Reactions in the presence of acetic acid are also examined.

Does the Cyclohehyl Cation Exist in the Dilute Gas State? Direct Evidence from a Radiolytic Study

The isomeric composition of the daseous C6H11+ cations obtained via hydride ion abstraction from c-C6H12 has been investigated by allowing the charged species to react in the gas phase with water and analyzing the neutral products formed.The nature and the yields of the major products, cyclohexanol, cyclohexanone, and 1-methylcyclopentanol, and their dependence on the pressure and the composition of the gaseous system provide direct evidence for the existence of the cyclohexyl cation in the dilute gas state, with a lifetime in excess of 10-7 s, and confirm its facile rearrangement to the more stable 1-methylcyclopentyl ion.