5116-65-4Relevant articles and documents
Syntheses and spectroscopic characterizations of oxidative metabolites of 4-vinylcyclohexene
Mash,Gregg,Sipes
, p. 235 - 239 (1994)
The 7,8-epoxide and 7,8-diol derivatives of 4-vinylcyclohexene were prepared and characterized spectroscopically for use as standards in toxicological studies of the oxidative metabolism of the parent hydrocarbon.
METHOD FOR PRODUCING EPOXY COMPOUND
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Paragraph 0089-0091, (2021/11/05)
The invention provides a method for producing an epoxy compound by hydrogen peroxide using an organic compound having a carbon-carbon double bond as a raw material, wherein a by-product is suppressed from being generated and the epoxy compound is produced in a high yield. In particular, the invention provides a method for producing an epoxy compound involving oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound; a phosphoric acid, a phosphonic acid or salts thereof; and an onium salt having an alkyl sulfate ion represented by formula (I) as an anion: wherein R1 is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbons, which may be substituted with 1 to 3 phenyl groups.
Carboranycarboxylate Complexes as Efficient Catalysts in Epoxidation Reactions
Fontanet, Mònica,Rodríguez, Montserrat,Vi?as, Clara,Teixidor, Francesc,Romero, Isabel
, p. 4425 - 4429 (2017/10/06)
This work presents the first examples of carboranylcarboxylate complexes as precatalysts in epoxidation reactions with the use of peracetic acid as the oxidant. The manganese [Mn(μ-H2O)(1-CH3-2-CO2-1,2-closo-C2B10H10)2]n·(H2O)n (1), [Mn2(1-CH3-2-CO2-1,2-closo-C2B10H10)4(2,2′-bpy)2] (2, bpy = bipyridine), [Mn(1-CH3-2-CO2-1,2-closo-C2B10H10)2(bpm)]n (3, bpm = bipyrimidine), and [Mn(1-CH3-2-CO2-1,2-closo-C2B10H10)2(2,2′-bpy)2] (4) complexes and the cobalt [Co2(μ-H2O)(1-CH3-2-CO2-1,2-closo-C2B10H10)4(thf)4] (6) complex, all containing the carboranylcarboxylic 1-CH3-2-CO2H-1,2-closo-C2B10H10 (LH) ligand, together with Mn3(OAc)6(2,2′-bpy)2 (5) displayed good performance with high conversions and selectivity values in short reaction times, in most cases. This work highlights that the coordination of the carboranylcarboxylic ligand to the metal ions is crucial to the performance of the complexes as catalysts.
New Ru(II) complexes containing oxazoline ligands as epoxidation catalysts. Influence of the substituents on the catalytic performance
Serrano, Isabel,Lopez, M. Isabel,Ferrer, Ingrid,Poater, Albert,Parella, Teodor,Fontrodona, Xavier,Sola, Miquel,Llobet, Antoni,Rodriguez, Montserrat,Romero, Isabel
experimental part, p. 6044 - 6054 (2011/09/13)
The synthesis of a family of new Ru complexes containing the facial tridentate ligand with general formula [RuII(T)(D)(X)]n+ (T = trispyrazolylmethane (tpm); D = ((4S,4′S)-(-)-4,4′,5,5′- tetrahydro-4,4′-bis(1-methylethyl)-2,2′-bioxazole) (iPr-box-C) or N-(1-hydroxy-3-methylbutan-(2S)-(-)-2-yl)-(4S)-(-)-4-isopropyl-4, 5-dihydrooxazole-2-carbimidate (iPr-box-O); X = Cl, H2O) has been described. All complexes have been spectroscopically characterized in solution through 1H NMR and UV-vis techniques, and the redox properties of complexes have also been studied by means of cyclic voltammetry (CV). Furthermore, the chloro complexes presented here have been characterized in the solid state through monocrystal X-ray diffraction analysis. The oxazolinic iPr-box-C ligand undergoes a Ru-assisted hydrolysis reaction generating the corresponding amidate anionic ligand iPr-box-O, that keeps coordinated to the Ru metal center and that produces a strong σ-donation effect over it. The reactivity of the Ru-OH2 complexes described in this paper together with other similar ones, previously synthesized by us, has been tested with regard to the epoxidation of different olefins. Complexes [Ru II(R-box-C)(tpm)OH2](BF4)2, R = Bz, 3′c/iPr, 3c, show high stereoselectivity in the epoxidation of cis-β-methylstyrene, with the exclusive formation of the cis-epoxide. However, there is a significant difference in regioselectivity between the two catalysts in the epoxidation of 4-vinylcyclohexene; complex 3′c leads to the regioselective oxidation at the ring alkene position, whereas complex 3c leads to the oxidation at the terminal position. Computational calculations indicate only small energy differences between the two possible products of 4-vinylcyclohexene epoxidation, but the energy barriers for the interaction of the catalytic systems with the alkene groups of 4-vinylcyclohexene agree with the reactivity differences found for the two catalysts having isopropyl or benzyl as substituent of the oxazole ligand. Computed local Fukui functions help to explain the observed reactivity trends.
