2808-79-9

Usage

InChI:InChI=1/C8H14/c1-7-3-5-8(2)6-4-7/h3,8H,4-6H2,1-2H3

Upstream product

• 64-18-6 formic acid 
• 16980-60-2 1,4-Dimethyl-cyclohexanol 
• 16980-61-3 trans-1,4-dimethylcyclohexan-1-ol 
• 5402-28-8 1,4-dimethylcyclohexan-1-ol 
• 106-42-3 para-xylene 
• 144-62-7 oxalic acid 
• 3809-32-3 2,5-dimethylcyclohexanol 
• 49570-30-1 1,4-dimethyl-2,3-diazabicyclo<2.2.2>oct-2-ene 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 71-43-2 benzene 
• 932-51-4 2,5-dimethylcyclohexanone 
• 589-92-4 1-methylcyclohexan-4-one 

Downstream Products

• 861538-31-0 1,4-dimethyl-cyclohexane-1,2-diol 
• 14845-35-3 2,5-dimethyl-cyclohex-2-enone 
• 91861-30-2 2,5-dimethyl-1-cyclohexen-1-yl 2-methyl-1-cyclopenten-1-yl ketone 
• 589-90-2 1,4 dimethylcyclohexane 
• 2207-04-7 trans-1,4-dimethylcyclohexane 
• 624-29-3 cis-1,4-dimethylcyclohexane 
• 106-42-3 para-xylene 
• 932-51-4 2,5-dimethylcyclohexanone 
• 922512-01-4 1-(4-methylphenyl)-1,4-dimethylcyclohexane 
• 18387-09-2 1-Dimethylamino-1,4-dimethyl-cyclohexanon-2-oxim 
• 91861-33-5 2-methyl-2-(1,4-dimethyl-2,4-cyclohexadien-1-yl)-cyclopentanenitrile 

Relevant academic research and scientific papers

Bond Memory in Dynamically Determined Stereoselectivity

The carboborative ring contraction of cyclohexenes exhibits an abnormal selectivity pattern in which a formally concerted double migration gives rise to predominant but not exclusive inversion products. In dynamic trajectories, the inversion and retention products are formed from the same transition state, and the trajectories accurately account for the experimental product ratios. The unusual origin of the selectivity is the dynamically retained non-equivalence of newly formed versus pre-existing bonds after the first bond migration.

Ligand effect in the Rh-NP catalysed partial hydrogenation of substituted arenes

The Rh nanoparticles Rh1-Rh4 stabilised by the mono- and bidentate phosphine and phosphite ligands I-IV were synthesised, characterised and applied as catalysts in the partial hydrogenation of substituted arenes. In the case of disubstituted arenes, selectivities for the corresponding cyclohexene derivatives of up to 39% were achieved at ca. 40% conversion. The effect of parameters such as temperature and pressure was also examined. In the hydrogenation of styrene, very high selectivities for ethylbenzene were achieved with TOF values up to ca. 23500 h-1. All these results show that the catalytic performance of small Rh-NPs can be modulated by the appropriate choice of stabilising agents.

Hydrogenation of arenes and N-heteroaromatic compounds over ruthenium nanoparticles on poly(4-vinylpyridine): A versatile catalyst operating by a substrate-dependent dual site mechanism

A nanostructured catalyst composed of Ru nanoparticles immobilized on poly(4-vinylpyridine) (PVPy) has been synthesized by NaBH4 reduction of RuCl3·3H2O in the presence of the polymer in methanol at room temperature. TEM measurements show well-dispersed Ru nanoparticles with an average diameter of 3.1 nm. Both powder XRD patterns and XPS data indicate that the Ru particles are predominantly in the zerovalent state. The new catalyst is efficient for the hydrogenation of a wide variety of aromatic hydrocarbons and N-heteroaromatic compounds representative of components of petroleum-derived fuels. The experimental data indicate the existence of two distinct active sites in the nanostructure that lead to two parallel hydrogenation pathways, one for simple aromatics involving conventional homolytic hydrogen splitting on Ru and a second one for N-heteroaromatics taking place via a novel heterolytic hydrogen activation on the catalyst surface, assisted by the basic pyridine groups of the support.

Unsaturated aldehydes as alkene equivalents in the Diels-Alder reaction

A one-pot procedure is described for using α,β-unsaturated aldehydes as olefin equivalents in the Diels-Alder reaction. The method combines the normal electron demand cycloaddition with aldehyde dienophiles and the rhodium-catalyzed decarbonylation of aldehydes to afford cyclohexenes with no electron-with-drawing substituents. In this way, the aldehyde group serves as a traceless control element to direct the cycloaddition reaction. The Diels-Alder reactions are performed in a diglyme solution in the presence of a catalytic amount of boron trifluoride etherate. Subsequent quenching of the Lewis acid, addition of 0.3% of [Rh(dppp)2Cl] and heating to reflux achieves the ensuing decarbonylation to afford the product cyclohexenes. Under these conditions, acrolein, crotonaldehyde and cinnamaldehyde have been reacted with a variety of 1,3-dienes to afford cyclohexenes in overall yields between 53 and 88%. In these transformations, the three aldehydes serve as equivalents of ethylene, propylene and styrene, respectively.

Ionic-liquid-like copolymer stabilized nanocatalysts in ionic liquids: II. Rhodium-catalyzed hydrogenation of arenes

Rhodium nanoparticles stabilized by the ionic-liquid-like copolymer poly[(N-vinyl-2-pyrrolidone)-co-(1-vinyl-3-butylimidazolium chloride)] were used to catalyze the hydrogenation of benzene and other arenes in ILs. The nanoparticle catalysts can endure forcing conditions (75 °C, 40 bar H2), resulting in high reaction rates and high conversions compared with other nanoparticles that operate in ILs. The hydrogenation of benzene attained record total turnovers of 20,000, and the products were easily separated without being contaminated by the catalysts. Other substrates, including alkyl-substituted arenes, phenol, 4-n-propylphenol, 4-methoxylphenol, and phenyl-methanol, were studied and in most cases were found to afford partially hydrogenated products in addition to cyclohexanes. In-depth investigations on reaction optimization, including characterization of copolymers, transmission electron microscopy, and an infrared spectroscopic study of nanocatalysts, were also undertaken.

(ALKYLPHENYL)ALKYLCYCLOHEXANE AND METHOD FOR PRODUCING (ALKYLPHENYL)ALKYLCYCLOHEXANE OR ALKYLBIPHENYL

Disclosed is a method for producing an (alkylphenyl)alkylcyclohexane comprising a step wherein an alkylbenzene and an alkylcyclohexene or alkylcyclohexanol are condensed in the presence of an acid catalyst. Also disclosed is an (alkylphenyl)alkylcyclohexane represented by the formula (8) below. An (alkylphenyl)alkylcyclohexane obtained by such a production method is converted into an alkylbiphenyl, a biphenylpolycarboxylic acid or a biphenylpolycarboxylic acid anhydride. This production method enables to easily and selectively obtain an (alkylphenyl)alkylcyclohexane and an alkylbiphenyl. (8) (In the formula, R1-4 represent an alkyl group having 1-4 carbon atoms, m represents an integer of 0-2, n' represents an integer of 2-5, and the other conditions are as defined in claim 18.)

Quantitative analyses of the seven isomeric 3,4- and 3,6-dimethylcyclohexenes by gas chromatography

Quantitative analyses of mixtures of the seven isomeric 3,4- and 3,6-dimethylcyclohexenes have been achieved by gas chromatography. Correlations of structure and absolute stereochemistry with elution order have been made rigorously with the aid of authentic optically active samples all derived from (3R)-methylcyclohexanone.

Deazetation of 1,4-Dimethyl-2,3-diazabicyclooct-2-ene: Stereochemistry and the Formation of Dimethylcyclohexene

Irradiation of stereospecifically labelled 2H2>-1,4-dimethyl-2,3-diazabicyclooct-2-ene gave 1,4-dimethylbicyclohexane and 2,5-dimethylhexa-1,5-diene with the label randomly distributed between the stereochemically differentiated positions, together with 1,4-dimethylcyclohexene, which was only formed in the direct photolysis.

Composition of Mixtures of Hydrocarbons after BIRCH-Reduction of Substituted Benzenes and Acid Catalyzed Addition of Alcohols to Alkylsubstituted Cyclohexenes and Carbohexa-1,4-dienes

10 different benzene hydrocarbons 1, indane, tetraline, anisol and phenol are reduced by sodium in liquid ammonia in the presence of methanol to the BIRCH products 2.The product mixture compositions are determined through capillary GLC.On storage at +6 deg C some rearomatization of the 1,4-cyclohexadienes 2 occurs.Data of the 1H- and 13C-.n.m.r. spectra and also mass spectra of the BIRCH 1,4-dienes 2 are given.For comparison 4-alkoxycyclohexenes 4 and 1-alkoxy-1-methylcyclohexanes 8 are prepared and spectroscopically characterized.Acid-catalyzed addition of alcohols to the 1,4-cyclohexadienes systems is a slow process and gives the 4-alkoxy-4-alkylcyclohex-1-enes (4) only in moderate yields up to 30percent.Most of the products are dimers 5 and also oligomers 6 of the parent hydrocarbons 2.

Functionalization of Saturated Hydrocarbons. Part 4. The Gif System for Selective Oxidation using Molecular Oxygen

Various systems for the selective oxidation of saturated hydrocarbons have been developed.These are based on the idea of an iron catalyst which is reduced by electron transfer and oxidized by molecular oxygen simultaneously in the presence of a source of protons.Four modifications of this system (the Gif system) have been devised of which the best (Gif IV) consists of an iron catalyst with metallic zinc as the reductant, acetic acid as the proton source and pyridine as the solvent.At room temperature, using oxygen or air, saturated hydrocarbons are oxidized selectively to ketones in isolated yields superior to those reported for comparable model systems.