56595-78-9

Upstream product

• 591-49-1 1-methylcyclohex-1-ene 
• 3426-71-9 Benzyl N-hydroxycarbamate 

Downstream Products

• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 16112-10-0 1-(cyclopent-1-en-1-yl)ethanone 
• 20461-30-7 2-methylcyclohex-2-en-1-ol 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 1193-18-6 3-methylcyclohexen-2-one 
• 36291-65-3 2-methyl-cyclohex-2-enone semicarbazone 
• 439667-21-7 1-methyl-cyclohexane-1,2,3-triol 

Relevant academic research and scientific papers

An entirely solvent-free photooxygenation of olefins under continuous flow conditions

Photooxygenations of alkenes with singlet oxygen are a versatile, atom-economical transformation. The choice of solvents is key to the success of this oxyfunctionalization with direct impact on the solubility of substrates, the lifetime of the reactive oxygen species, and the up-scaling of the process. We report an entirely solvent-free continuous-flow photooxygenation that operates at very high substrate/sensitizer ratios and enables high space-time yields.

Organic Dye-Photocatalyzed Acylnitroso Ene Reaction

Rose bengal, an inexpensive and readily available organic dye, is demonstrated to be a photoredox catalyst for the formation of transient acylnitroso intermediates under visible light irradiation. This method is operationally simple and uses air as the te

Strategies for cleaner oxidations using photochemically generated singlet oxygen in supercritical carbon dioxide

Photochemically generated singlet oxygen, 1O2, has been reacted with four different substrates in supercritical carbon dioxide. By using fluorous surfactants and a co-solvent to solubilise more polar photosensitisers and reactants respectively, the applicability of the system is greatly enhanced. The Royal Society of Chemistry 2009.

9-Mesityl-10-methylacridinium: An efficient type II and electron-transfer photooxygenation catalyst

The visible-light irradiation of 9-mesityl-10-methylacridinium perchlorate 1 in the presence of monoalkenes and molecular oxygen leads to typical products of singlet oxygen addition (type II photooxygenation). The molecular probes 1-methylcyclohexene and limonene, respectively, result in hydroperoxide mixtures with a characteristic product pattern. A switch in the oxidative mechanism (electron-transfer photooxygenation) is observed for naphthalene derivatives as electron-rich acceptor molecules, revealing that the 9-mesityl-10- methylacridinium cation serves as a dual sensitizer with the capacity of efficient singlet oxygen formation and electron-transfer reaction.

Controlling photoreactions with restricted spaces and weak intermolecular forces: Exquisite selectivity during oxidation of olefins by singlet oxygen

Highly regioselective photooxidation of methyl cycloalkenes has been performed in an aqueous medium by selectively blocking two of the three allylic hydrogens through supramolecular steric effect. Hydrophobic, steric, and weak intermolecular C-H-π interac

Glycol-modified molybdate catalysts for efficient singlet oxygen generation from hydrogen peroxide

Pretreatment of molybdate-exchanged layered double hydroxides in polyalcohols such as ethylene glycol affords heterogeneous catalysts showing largely improved oxidant efficiency compared to the unmodified materials. The Royal Society of Chemistry.

Ring-opening metathesis polymer sphere-supported seco-porphyrazines: Efficient and recyclable photooxygenation catalysts

Crossover Linstead macrocyclization of norbornenyl-tagged diaminomaleonitrile with dipropylmaleonitrile gave the corresponding magnesium diaminohexapropylporphyrazine, which was subsequently converted into its zinc seco-derivative. Polymerization gave the corresponding ROMPgel and ROMPsphere (ROMP = ring-opening metathesis polymer) reagents, the latter of which proved efficient as an immobilized catalyst for the sensitized production of singlet oxygen for the purification-minimized parallel synthesis of endoperoxides and ene adducts.

Visible-light induced solvent-free photooxygenations of organic substrates by using [60]fullerene-linked silica gels as heterogeneous catalysts and as solid-phase reaction fields

Novel recyclable heterogeneous catalysts generating singlet-oxygen under visible-light irradiation have been prepared by linking [60]fullerene to amino-functionalized silica gels. The catalysts facilitate various types of photooxygenerations including Diels-Alder reaction, ene reaction, and oxidations of phenol and sulfide in a solid-solvent system and even in a solvent-free system.

PROCESS FOR OXIDIZING ORGANIC SUBSTRATES BY MEANS OF SINGLET OXYGEN USING A MODIFIED MOLYBDATE LDH CATALYST

Oxidation of organic substrates by means of singlet oxygen, in which organic substrates which react with 1O2 are admixed with 10-70% H2O2 in an organic solvent in the presence of a molybdate LDH catalyst modified by ethylene glycol, polyethylene glycol or polyol, and the catalytic decomposition of H2O2 to water and 1O2 is then followed by the oxidation to the corresponding oxidation products, and also modified molybdate LDH catalysts.

Confined space-controlled hydroperoxidation of trisubstituted alkenes adsorbed on pentasil zeolites

Photosensitized oxidation of trialkylalkenes 2-methyl-2-pentene (1), 1-methylcyclohexene (2), trans-3-methyl-2-pentene (3), cis-3-methyl-2-pentene (4), and 2-methyl-2-butene (5) included in the internal framework of Na-ZSM-5 zeolites was investigated. The zeolite samples having adsorbed the alkenes were suspended in isooctane, and the sensitizer, tetraphenylporphyrin (TPP), was dissolved in the solution. Singlet oxygen produced in the solution diffused into the internal framework of the zeolites and reacted with alkenes. For all the substrates studied, the ene-type allylic hydroperoxides were obtained in a highly regioselective manner. The regiochemistry for 1-4 in favor of the allylic hydrogen abstraction from the largest substituents is in contrast to their photooxidation within the dye-supported zeolite Na-Y, where the secondary hydroperoxides are preferentially produced. The tight confinement of the alkenes within the narrow channels of the ZSM-5 zeolites is likely to be responsible for this selectivity.