115667-79-3

Upstream product

• 13389-42-9 trans-2-Octene 
• 7642-04-8 cis-2-octene 
• 111-67-1 2-octene 
• 108-24-7 acetic anhydride 

Downstream Products

• 13389-42-9 trans-2-Octene 
• 69814-27-3 (2S,3R)-3-Methylselanyl-octan-2-ol 
• 69814-37-5 (2S,3R)-2-Methylselanyl-octan-3-ol 
• 103941-98-6 2-methyloctane-1,3-diol 
• 104358-18-1 3-hydroxymethyl-2-octanol 
• 7642-04-8 cis-2-octene 
• 66-25-1 hexanal 

Relevant academic research and scientific papers

Reactivities of Acylperoxy Radicals in the Photoreaction of α-Diketones and Oxygen

The photoepoxidation of olefins with α-diketones and oxygen has been studied mechanistically focusing on the reactivities of intermediate radicals.One mole of α-diketone resulted in the formation of 2 mol of epoxide together with 2 equiv of C-C cleavage of olefins.The photoepoxidation proceeds via acylperoxy radicals RCO3* and the C-C cleavage of olefins is caused by acyloxy radical RCO2*.The addition of RCO3* to olefins was found to be ca.105-fold faster than that of acylperoxy radical ROO*.The relative reactivities of olefins suggest that acylperoxy radicals behave as a strongly electrophilic radical.That is, ρ values of -1 (vs.?+) obtained in the photoepoxidation of substituted styrenes are of the same magnitude as those in the epoxidation with molecular peracids.Although the relative reactivities of olefins toward the photoepoxidation roughly parallel those for the peracid epoxidations, the additivity of methyl substituent is not always operative.This is explained by a steric retardation by too many substituents on the carbon attacked by RCO3* in addition to the relative stabilities of resulting adduct radicals between olefins and RCO3*.Since acylperoxy radicals are not reactive towards sulfides, sulfoxides, or pyridine, a selective epoxidation of double bonds is possible.The relative reactivities of olefins toward benzoyloxy and methylperoxy redicals revealed a much less electrophilic nature of these oxy radicals, the ρ values for styrenes being -0.1 to -0.2.

An efficient epoxidation of terminal aliphatic alkenes over heterogeneous catalysts: When solvent matters

The epoxidation of unfunctionalized terminal aliphatic alkenes over heterogeneous catalysts is still a challenging task. Due to the tuning of a peculiar catalyst/oxidant/solvent combination, it was possible to attain good alkene conversions (73%) and excellent selectivity values (>98%) in the desired terminal 1,2-epoxide. Over the titanium-silica catalyst and in the presence of tert-butylhydroperoxide, the use of α,α,α-trifluorotoluene as an uncommon non-toxic solvent was the key factor for a marked enhancement of selectivity. The titanium-silica catalyst was efficiently recycled and reused after a gentle rinsing with fresh solvent.

Cobalt(II) Catalysed Epoxidation of Unfunctionalised Alkenes with in Situ Generated Hydroperoxide from Methyl-2-oxocyclopentane Carboxylate and Molecular Oxygen

Cobalt(II) complex 1 catalyses the epoxidation of unfunctionalised alkenes by in situ generated hydroperoxide from methyl-2-oxo-cyclopentane carboxylate and molecular oxygen.

Deracemization of (±)-2,3-disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases: Kinetics of an enantioconvergent process

Asymmetric biocatalytic hydrolysis of (±)-2,3-disubstituted oxiranes leading to the formation of vicinal diols in up to 97% ee at 100% conversion was accomplished by using the epoxide hydrolase activity of various bacterial strains. The mechanism of this deracemization was elucidated by 18OH2-labelling experiments using a partially purified epoxide hydrolase from Nocardia EH1. The reaction was shown to proceed in an enantioconvergent fashion by attack of OH- at the (S)-configured oxirane carbon atom with concomitant inversion of configuration. A mathematical model developed for the description of the kinetics was verified by the determination of the four relative rate constants governing the regio- and enantio-selectivity of the process.

Mn(III)-Porphyrin Containing Heterogeneous Catalyst based on Microporous Polymeric Constituents as a New Class of Catalyst Support

Mn(III)-porphyrin containing #heterogeneous catalyst based on microporous polymeric constituents as a new class of #catalyst support from Korea University and Seoul National University of Science and Technology.

Dinuclear ru-aqua complexes for selective epoxidation catalysis based on supramolecular substrate orientation effects

Ru-aqua complex {[RuII(trpy)(H2O)] 2(μ-pyr-dc)}+ is a powerful epoxidation catalyst for a wide range of linear and cyclic alkenes. High turnover numbers (TNs), up to 17000, and turnover frequencies (TOF), up to 24120 h-1 (6.7 s -1), have been obtained using PhIO as oxidant. This species presents an outstanding stereospecificity for both cis and trans olefins towards the formation of their corresponding cis and trans epoxides. In addition, it shows different reactivity to cis and trans olefins due to a substrate orientation supramolecular effect transmitted by its ligand scaffold. This effect together with the impressive reaction rates are rationalized using electrochemical techniques and DFT calculations. A new Ru-aqua complex that behaves as a powerful epoxidation catalyst for a wide range of linear and cyclic alkenes is reported. High turnover numbers and frequencies are obtained by using PhIO as oxidant. The complex shows an outstanding stereospecificity for both cis and trans olefins towards the formation of their corresponding cis and trans epoxides (see figure).

Guanidinium-based phosphotungstates and ionic liquids as catalysts and solvents for the epoxidation of olefins with hydrogen peroxide

Several penta- and hexaalkylated guanidinium-based ionic liquids (GILs) were tested as solvents for the epoxidation of cyclooctene using the Venturello catalyst, [(C8H17)3N(CH3)] 3[PO4{WO(O2)2}4], and hydrogen peroxide as the oxidant. Epoxide yields were obtained in a broad range between 13 and 79 % depending on both the anion and the substituents on the guanidinium moiety. Recycling experiments showed that the catalyst can be used at least three times. Furthermore, new guanidinium phosphotungstates with the PW12O403- anion were synthesized and characterized. Their catalytic performance was evaluated, and GILs as well as acetonitrile were employed as the solvent. Results were compared to those obtained with the comparable ammonium-based catalysts [NR4] 3[PW12O40] (R = C4H9, C6H13) and the analogous imidazolium-based catalyst [BMIM]3[PW12O40] containing the 1-butyl-3-methylimidazolium cation. Employing different GILs as solvents, similar results were obtained for the guanidinium and imidazolium catalysts but significantly lower epoxide yields were obtained using the ammonium catalysts. On using acetonitrile as the solvent, guanidinium-based catalysts exhibited a better performance than the imidazolium catalyst in the case of linear and branched olefins and vice versa in the case of cyclic olefins. Several guanidinium phosphotungstates and guanidinium-based ionic liquids have been synthesized and characterized. Their catalytic performance in epoxidation reactions with hydrogen peroxide was evaluated and compared to similar ammonium and imidazolium compounds. The reaction systems can be recycled and used in at least three consecutive reactions. Copyright

Surface-mediated reactions. 5. Oxidation of sulfides, sulfoxides, and alkenes with tert-butyl hydroperoxide

Silica gel mediates the reactivity of (CH3)3COOH, affording a convenient, environmentally benign method for oxidizing sulfides, sulfoxides, and alkenes. Electrophilic oxidation of sulfides and alkenes (Scheme 1A) and nucleophilic oxidation of sulfoxides (Scheme 1B) are apparently involved. Basic alumina mediates the oxidation of sulfoxides.

Powerful Bis-facially Pyrazolate-Bridged Dinuclear Ruthenium Epoxidation Catalyst

A new bis-facial dinuclear ruthenium complex, {[RuII(bpy)]2(μ-bimp)(μ-Cl)}2+, 22+, containing a hexadentate pyrazolate-bridging ligand (Hbimp) and bpy as auxiliary ligands has been synthesized and fully characterized in solution by spectrometric, spectroscopic, and electrochemical techniques. The new compound has been tested with regard to its capacity to oxidize water and alkenes. The in situ generated bis-aqua complex, {[RuII(bpy)(H2O)]2(μ-bimp)}3+, 33+, is an excellent catalyst for the epoxidation of a wide range of alkenes. High turnover numbers (TN), up to 1900, and turnover frequencies (TOF), up to 73 min-1, are achieved using PhIO as oxidant. Moreover, 33+ presents an outstanding stereospecificity for both cis and trans olefins toward the formation of their corresponding epoxides due to specific interactions transmitted by its ligand scaffold. A mechanistic analysis of the epoxidation process has been performed based on density functional theory (DFT) calculations in order to better understand the putative cooperative effects within this dinuclear catalyst. (Figure Presented).

Selective Oxidation with Aqueous Hydrogen Peroxide by [PO4{WO(O2)2}4]3- Supported on Zinc-Modified Tin Dioxide

We prepared supported phosphorus-containing tetranuclear peroxotungstate ([PO4{WO(O2)2}4]3-, denoted by PW4) catalysts by using zinc-modified SnO2 supports with different zinc contents [PW4-Zn(x)/SnO2, in which x denotes the zinc content (wt%)]. The supported catalysts, in particular PW4-Zn(0.8)/SnO2, could act as efficient and reusable heterogeneous catalysts for selective oxidation with aqueous H2O2 as the terminal oxidant. The catalytic performance of PW4-Zn(0.8)/SnO2 was much superior to those of the corresponding homogeneous analogue THA3PW4 (THA=tetra-n-hexylammonium) and the previously reported tungstate-based heterogeneous catalysts such as our W-Zn/SnO2. In the presence of PW4-Zn(0.8)/SnO2, various types of organic substrates such as alkenes, amines, silanes, and sulfides could be converted into the corresponding oxygenated products in high to excellent yields by using near-stoichiometric amounts of H2O2 with respect to the substrates (typically 1.2 equiv.). The PW4 species interacting with highly dispersed Zn2+ species on SnO2 likely plays an important role in the present oxidation.