16529-03-6

Upstream product

• 2114-42-3 allylcyclohexane 
• 39972-78-6 allyl t-butyl peroxide 
• 110-82-7 cyclohexane 
• 143771-75-9 ethyl 2-[1-(1,1-dimethylethylperoxy)ethyl]propenoate 
• 4436-24-2 1,2-epoxy-3-phenylpropane 

Downstream Products

• 4361-28-8 3-cyclohexylpropanal 
• 1370019-53-6 (S)-N-butyl-N-(2-(cyclohexylmethyl)-5-(2-methoxyphenyl)pentyl)-4-methylbenzenesulfonamide 
• 1370019-74-1 N-butyl-N-(3-cyclohexyl-2-hydroxypropyl)-4-methylbenzenesulfonamide 
• 1370019-45-6 (S)-phenyl 2-(cyclohexylmethyl)-5-o-tolylpentyl(methyl)carbamate 

Relevant academic research and scientific papers

Rhodium nanoparticles supported on carbon nanofibers as an arene hydrogenation catalyst highly tolerant to a coexisting epoxido group

Rhodium nanoparticles supported on a carbon nanofiber (Rh/CNF-T) show high catalytic activity toward arene hydrogenation under mild conditions in high turnover numbers without leaching the Rh species; the reaction is highly tolerant to epoxido groups, which often undergo ring-opening hydrogenation with conventional catalysts.

A simple and effective catalytic system for epoxidation of aliphatic terminal alkenes with manganese(II) as the catalyst

A simple catalytic system that uses commercially available manganese(II) Perchlorate as the catalyst and peracetic acid as the oxidant is found to be very effective in the epoxidation of aliphatic terminal alkenes with high product selectivity at ambient temperature. Many terminal alkenes are epoxidised efficiently on a gram scale in less than an hour to give excellent yields of isolated product (>90%) of epoxides in high purity. Kinetic studies with some C9-alkenes show that the catalytic system is more efficient in epoxidising terminal alkenes than internal alkenes, which is contrary to most commonly known epoxidation systems. The reaction rate for epoxidation decreases in the order: 1-nonene>cis-3-nonene> trans-3-nonene. ESI-MS and EPR spectroscopic studies suggest that the active form of the catalyst is a high-valent oligonuclear manganese species, which probably functions as the oxygen atomtransfer agent in the epoxidation reaction.

A simple and efficient method for epoxidation of terminal alkenes

The use of a catalytic amount of 3-cyanopyridine in the methyltrioxorhenium catalysed epoxidation of terminal alkenes with aqueous hydrogen peroxide speeds turnover, which results in the formation of many functionalized epoxides in high yields.

Intramolecular Homolytic Displacements. Part 22. Polar Effects in the Homolytic Induced Decompositions of Allyl Peroxides

The products of the decomposition of allyl peroxides 1-5, initiated by tert-butyl peracetate, in three solvents - cyclohexane, dimethyl malonate and benzene - were analysed.The formation of epoxides proved the existence of an homolytic induced decomposition of the unsaturated peroxides by a chain process involving a free radical addition to the double bond and an intramolecular homolytic substitution on the peroxide linkage.The balance of the reaction's products indicated a second way of degradation of the peroxides: allylic hydrogen abstraction followed by the breaking of the peroxide bond by β-elimination.The relative ratios of the products generated by the eliminated alkoxy radicals YO(radical) and of the different epoxides produced in these reactions showed the influence of the polar factors in the various steps of the homolytic induced decomposition: i.e. hydrogen abstraction to the solvent or to the peroxide and addition to the double bond.

DEPLACEMENTS HOMOLYTIQUES INTRAMOLECULAIRES: 15 - ADDITIONS RADICALAIRES A DES PEROXYDES β-ETHYLENIQUES

Free radical additions of cyclohexane, tetrahydrofuran, methyl propanoate, acetonitrile, dichloromethane to allyl t-butyl peroxide, t-butyl 2-methyl prop-2-enyl peroxide, t-butyl 2,2-dimethyl prop-2-enyl peroxide and t-butyl 3-methyl but-2-enyl peroxide h

DEPLACEMENTS HOMOLYTIQUES INTRAMOLECULAIRES III-DECOMPOSITION DU PEROXYDE D'ALLYLE ET DE t-BUTYLE DANS LES ETHERS ET LES CYCLANES: EPOXY-2,3 PROPANATION DE CES SOLVANTS

Product analysis of the thermolysis of allyl t-butyl peroxide in cyclohexane and tetrahydrofuran shows that an important induced decomposition of the peroxide occurs by the addition of radicals derived from the solvent, to the peroxide double bond, followed by an intramolecular homolytic displacement of the t-butoxyl group.Such a reaction is a 2,3-epoxypropanation of the solvent in which the initiator is decomposed.The reaction is shown to be general, by using other ethers and cycloalkanes as solvents.

Addition radicalaire au peroxyde d'allyle et de t-butyle: synthese d'epoxydes fonctionnels

The free radical addition of labile hydrogen solvents to allyl and t-butyl peroxide led to 2,3-epoxypropanation of such compounds with yield over 50percent.

INTRAMOLECULAR HOMOLYTIC DISPLACEMENTS 7 - FREE RADICAL ADDITIONS TO UNSATURATED PEROXY COMPOUNDS : SYNTHESIS OF OXYGENATED HETEROCYCLES

Free radical additions of hydrogen donor solvents to tert-butyl perpent-4-enoate have given 4-substituted γ-butyrolactones, with yields of 50 percent or greater.Such reactions applied to allyl-tert-butyl peroxide have produced 2,3-epoxypropanation of these solvents.Similar addition-elimination processes occurred with tert-butyl 4-methyl-perpent-4-enoate, tert-butyl 2,2-dimethyl-perpent-4-enoate and tert-butyl-methallyl peroxide, but they failed with tert-butyl 5-methyl-perhex-4-enoate and tert-butyl-3-methyl-but-2-enyl peroxide.