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Cas Database

2085-88-3

2085-88-3

Identification

  • Product Name:Oxirane,2-methyl-2-phenyl-

  • CAS Number: 2085-88-3

  • EINECS:

  • Molecular Weight:134.178

  • Molecular Formula: C9H10 O

  • HS Code:2910900090

  • Mol File:2085-88-3.mol

Synonyms:Cumene, a,b-epoxy- (6CI,7CI,8CI); (?à)-2-Methyl-2-phenyloxirane; 1,2-Epoxy-2-phenylpropane;2-Methyl-2-phenyloxirane; 2-Phenyl-1,2-epoxypropane; 2-Phenyl-2-methyloxirane;2-Phenylpropene oxide; NSC 36616; NSC 51065; a-Methylstyrene epoxide; a-Methylstyrene oxide

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Safety information and MSDS view more

  • Signal Word:Danger

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation H340 May cause genetic defects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:α-MethylstyreneOxide
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Phenylpropylene Oxide >95.0%(GC)
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:α-MethylstyreneOxide
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Phenylpropylene Oxide 97%
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  • Product Description:2-Phenylpropylene Oxide 97%
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  • Manufacture/Brand:Crysdot
  • Product Description:2-Methyl-2-phenyloxirane 95+%
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  • Product Description:2-Methyl-2-phenyloxirane 95+%
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  • Manufacture/Brand:Atlantic Research Chemicals
  • Product Description:2-Phenylpropylene Oxide 95%
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  • Manufacture/Brand:Apolloscientific
  • Product Description:2-Phenylpropylene Oxide 95%
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Relevant articles and documentsAll total 365 Articles be found

A graphene oxide immobilized Cu(ii) complex of 1,2-bis(4-aminophenylthio)ethane: An efficient catalyst for epoxidation of olefins with tert-butyl hydroperoxide

Zarnegaryan, Ali,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammdpoor-Baltork, Iraj

, p. 2280 - 2286 (2016)

In this work, a new, recoverable and heterogeneous catalyst was prepared by covalent attachment of the Cu(ii) complex of 1,2-bis(4-aminophenylthio)ethane onto graphene oxide via the amide linkages. The structural and chemical nature of the catalyst was characterized by a variety of techniques such as Fourier transform infrared and diffuse reflectance UV-visible spectroscopies, X-ray diffraction, thermogravimetric analysis, transmission electron microscopy, field emission scanning electron microscopy and inductively coupled plasma atomic emission spectroscopy. The catalytic activity of this catalyst was investigated in the epoxidation of olefins with tert-butyl hydroperoxide. The catalyst has great reusability and stability in the epoxidation reactions.

Copper(II) Schiff base complex immobilized on graphene nanosheets: a heterogeneous catalyst for epoxidation of olefins

Zarnegaryan, Ali,Pahlevanneshan, Zari,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammdpoor-Baltork, Iraj

, p. 747 - 756 (2019)

The present paper describes the preparation and characterization of Cu(II) Schiff base complex immobilized onto graphene oxide. The structural and morphological characterization of the heterogeneous catalyst was carried out by different techniques such as Fourier transform infrared and diffuse reflectance UV–Vis spectroscopies, X-ray diffraction, thermogravimetric analysis, nitrogen adsorption–desorption, transmission electron microscopy, field emission scanning electron microscopy and inductively coupled plasma atomic emission spectroscopy. The catalytic activity of the heterogeneous catalyst was studied in the epoxidation of various alkenes using tert-butyl hydroperoxide as an oxidant and it showed high selectivity and catalytic reactivity. The graphene-bound copper Schiff base was successfully reused for several runs without significant loss in its catalytic activity.

m-Chloroperoxybenzoic Acid-Potassium Fluoride System: Study of Its Stability and Reaction with α-Methylstyrene

Camps, F.,Coll, J.,Messeguer, A.,Pujol, F.

, p. 5402 - 5404 (1982)

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Manganese meso-tetra-4-carboxyphenylporphyrin immobilized on MCM-41 as catalyst for oxidation of olefins with different oxygen donors in stoichiometric conditions

Rayati, Saeed,Zakavi, Saeed,Jafarzadeh, Parisa,Sadeghi, Omid,Amini, Mostafa M.

, p. 260 - 266 (2012)

Oxidation of olefins with tert-butyl hydroperoxide (TBHP), tetra-n-butylammonium periodate (TBAP) and potassium peroxomonosulfate (Oxone) in the presence of MCM-41 immobilized meso-tetra-4- carboxyphenylporphyrinatomanganese(III) acetate has been studied.

Molybdenum Schiff base-polyoxometalate hybrid compound: A heterogeneous catalyst for alkene epoxidation with tert-BuOOH

Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Javadi, Maedeh Moshref

, p. 648 - 654 (2010)

The hybrid compound consisting of molybdenum(salen) [salen = N,N′-bis(salicylidene)ethylnediamine] complex covalently linked to a lacunary Keggin-type polyoxometalate, K8[SiW11O39] (POM), was synthesized and characterized by elemental analysis, FT-IR, 1H NMR and diffuse reflectance UV-Vis spectroscopic methods and BET analysis. The complex, [Mo(O)2(salen)-POM], was studied, for the first time, in the epoxidation of various alkenes with tert-BuOOH and in 1,2-dichloroethane as solvent. This catalyst can catalyze epoxidation of various olefins including non-activated terminal olefins. The effect of the other parameters such as solvent, oxidant and temperature on the epoxidation of cyclooctene was also investigated. The interesting characteristic of this catalyst is that, in addition to being a heterogeneous catalyst, it gives higher yields towards epoxidation of olefins in comparison to the corresponding homogeneous [Mo(O)2(salen)] complex.

Efficient and selective hydrocarbon oxidation with sodium periodate catalyzed by supported manganese(III) porphyrin

Tangestaninejad,Moghadam,Mirkhani,Mohammadpoor-Baltork,Hoseini

, p. 663 - 672 (2010)

Manganese(III) tetrakis(p-sulfonatophenyl)porphyrin was successfully bound to silica modified with zirconium. The heterogeneous catalyst, MnTPPS-silica, was characterized by SEM, FT-IR and diffuse reflectance UV-Vis spectroscopic techniques. MnTPPS-silica catalyzes alkene epoxidation and alkanes hydroxylation with sodium periodate under agitation with magnetic stirring and ultrasonic irradiation in the presence of imidazole as an axial ligand. This catalytic system shows a good activity in the epoxidation of linear alkenes. Alkyl aromatic and cycloalkanes were efficiently oxidized to their corresponding alcohols and ketones in the presence of this catalyst. This new heterogeneous catalyst is of high stability and reusability in the oxidation reactions and can be reused several times without loss of its activity.

Cleavage of the Carbon-Carbon Double Bond over Zeolites using Hydrogen eroxide

Reddy, J. Sudhakar,Khire, Uday R.,Ratnasamy, P.,Mitra, Rajat B.

, p. 1234 - 1235 (1992)

Zeolite molecular sieves catalyse the cleavage of carbon-carbon double bonds of various alkenes in the presence of aqueous hydrogen peroxide as an oxidant; titanium silicate molecular sieves, TS-1 and TS-2 exhibit very high activity in the conversion of α-methylstyrene into acetophenone.

-

Yano et al.

, p. 527 (1973)

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Dialkyl peroxides decomposition in the presence of quaternary ammonium halides

Maksyuta,Suprun,Opeida,Turovskii

, p. 814 - 818 (2001)

Decomposition of dicumyl peroxide and cumyl tert-butyl peroxide was studied in the presence of tetraethylammonium halides in acetonitrile, dimethylformamide, 2-propanol, and acetic acid. The tetraethylammonium halides accelerate the decomposition of dialkyl peroxides in 2-propanol and acetic acid, but do not affect the reaction velocity in dimethylformamide and acetonitrile. The decomposition products character depends on the solvent nature.

Multi-wall carbon nanotube supported tungsten hexacarbonyl: An efficient and reusable catalyst for epoxidation of alkenes with hydrogen peroxide

Nooraeipour, Mehdi,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Iravani, Nasir

, p. 226 - 238 (2012)

Highly efficient epoxidation of alkenes with H2O2 catalyzed by tungsten hexacarbonyl supported on multi-wall carbon nanotubes (MWCNTs) modified with 1,2-diaminobenzene is reported. The prepared catalyst, [W(CO)6@DAB-MWCNT], was characterized by elemental analysis, scanning electron microscopy, FT-IR, and diffuse reflectance UV-Vis spectroscopic methods. The prepared catalyst was applied as an efficient catalyst for green epoxidation of alkenes with hydrogen peroxide in CH3CN. This heterogeneous metal carbonyl catalyst showed high stability and reusability in epoxidation without loss of its catalytic activity. Copyright

Enhancement of the photoinduced oxidation activity of a ruthenium(II) complex anchored on silica-coated silver nanoparticles by localized surface plasmon resonance

Mori, Kohsuke,Kawashima, Masayoshi,Che, Michel,Yamashita, Hiromi

, p. 8598 - 8601 (2010)

Plasmonic photocatalyst: Anchoring the dye [Ru(bpy)3] 2+ (bpy=2,2-bipyridine) on the surface of Ag nanoparticles coated with a thin SiO2 layer (see picture) afforded a photocatalyst whose phosphorescence emission and photoinduced oxidation activity in the selective liquid-phase oxidation of styrene are efficiently enhanced through interaction with the localized surface plasmon resonance of the core Ag nanoparticles.

New molybdenum(VI) complexes with thiazole-hydrazone ligand: Preparation, structural characterization, and catalytic applications in olefin epoxidation

Ghorbanloo, Massomeh,Bikas, Rahman,Ma?ecki, Grzegorz

, p. 8 - 16 (2016)

The reaction of [MoO2(acac)2] with (E)-2-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)-6-methoxyphenol (H2L), in acetonitrile and ethanol resulted in the formation of {[MoO2(HL)(H2O)]2[Mo6O19]·2MeCN} (1) (mononuclear cationic complex with hexamolybdate anion) and [MoO2L(EtOH)] (2) (neutral mononuclear complex), depending on the reaction conditions. In these compounds, the ligand is coordinated to the cis-MO22+ core via phenolic-oxygen, thiazole and azomethine nitrogen atoms, while the remaining sixth coordination site is occupied by the oxygen atom from the solvent molecule. Crystal and molecular structures of the compounds 1 and 2 were determined by the single crystal X-ray diffraction method. All of the investigated compounds were further characterized by elemental analysis, FT-IR and NMR spectroscopy. The molybdenum(VI) species were used as catalyst for olefin oxidation in the presence of tert-butylhydroperoxide (TBHP) as an oxidant. Under similar experimental conditions with equal Mo loading, the presence of the {[MoO2(HL)(H2O)]2[Mo6O19]·2MeCN} (1) resulted in higher oxidation conversion than [MoO2L(EtOH)] (2). It seems 1 contains two potentially active parts, the [MoO2(HL)H2O]+ cation and the Mo6O19?2 anion.

Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism

Mori, Tadashi,Takamoto, Makoto,Tate, Yoshimasa,Shinkuma, Junya,Wada, Takehiko,Inoue, Yoshihisa

, p. 2505 - 2508 (2001)

α-Methylstyrene (1) was photooxidized with oxygen in the presence of a series of alkylated dimethoxybenzenes as a sensitizer in acetonitrile, affording the cleaved ketone (2), epoxide (3) as well as a small amount of the ene product (4) in ca. 1:1:0.04 ratio. A non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by oxygen to produce a sensitizer radical cation and a superoxide ion (O2·-), the former of which oxidizes 1, while O2·- reacts with the resulting 1·+ to give the major oxidation products.

Hybrid mesoporous-silica materials functionalized by PtII complexes: Correlation between the spatial distribution of the active center, photoluminescence emission, and photocatalytic activity

Mori, Kohsuke,Watanabe, Kentaro,Terai, Yoshikazu,Fujiwara, Yasufumi,Yamashita, Hiromi

, p. 11371 - 11378,8 (2012)

[Pt(tpy)Cl]Cl (tpy: terpyridine) was successfully anchored to a series of mesoporous-silica materials that were modified with (3-aminopropyl) triethoxysilane with the aim of developing new inorganic-organic hybrid photocatalysts. Herein, the relationship between the luminescence characteristics and photocatalytic activities of these materials is examined as a function of Pt loading to define the spatial distribution of the Pt complex in the mesoporous channel. At low Pt loading, the Pt complex is located as an isolated species and exhibits strong photoluminescence emission at room temperature owing to metal-to-ligand charge-transfer (3MLCT) transitions (at about 530 nm). Energy- and/or electron-transfer from 3MLCT to O2 generate potentially active oxygen species, which are capable of promoting the selective photooxidation of styrene derivatives. On the other hand, short Pt...Pt interactions are prominent at high loading and the metal-metal-to-ligand charge-transfer (3MMLCT) transition is at about 620 nm. Such Pt complexes, which are situated close to each other, efficiently catalyze H2-evolution reactions in aqueous media in the presence of a sacrificial electron donor (EDTA) under visible-light irradiation. This study also investigates the effect of nanoconfinement on anchored guest complexes by considering the differences between the pore dimensions and structures of mesoporous-silica materials. Anchorman: [Pt(tpy)Cl]Cl (tpy: terpyridine) was anchored to a series of mesoporous-silica materials that were modified with (3-aminopropyl)trimethoxysilane to afford new inorganic-organic hybrid photocatalysts (see graphic). Copyright

An efficient biomimetic Fe-catalyzed epoxidation of olefins using hydrogen peroxide

Anilkumar, Gopinathan,Bitterlich, Bianca,Gelalcha, Feyissa Gadissa,Tse, Man Kin,Beller, Matthias

, p. 289 - 291 (2007)

A new, environmentally benign and practical epoxidation method was developed using inexpensive and efficient Fe catalysts. FeCl3· 6H2O in combination with commercially available pyridine-2,6- dicarboxylic acid and amines showed excellent reactivity and selectivity towards aromatic olefins and moderate reactivity towards 1,3-cyclooctadiene utilizing H2O2 as the terminal oxidant. The Royal Society of Chemistry.

Synthesis, structural characterization and catalytic potential of oxidovanadium(IV) and dioxidovanadium(V) complexes with thiazole-derived NNN-donor ligand

Ghorbanloo, Massomeh,Bikas, Rahman,Jafari, Solmaz,Krawczyk, Marta S.,Lis, Tadeusz

, p. 1510 - 1525 (2018)

Reaction between the tridentate NNN donor ligand, (E)-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)benzo[d]thiazole (HL), and V2O5 in ethanol gave a new vanadium(V) complex, [VO2L] (1), while the similar reaction by using [VIVO(acac)2] as the metal source gave two different types of crystals related to compounds [VO2L] (1) and [VIVO(acac)L] (2). The molecular structures of the complexes were determined by single-crystal X-ray diffraction and spectroscopic characterization was carried out by means of FT-IR, UV–vis and NMR experiments as well as elemental analysis. The oxidovanadium(IV) and dioxidovanadium(V) species were used as catalyst precursors for olefin oxidation in the presence of hydrogen peroxide (H2O2) as an oxidant. Under similar experimental conditions, the presence of 1 resulted in higher oxidation conversion than 2.

The in situ generation and use of iodomethyllithium for the one-carbon homologation of boronic esters and epoxide formation from carbonyl compounds

Wallace,Battle

, p. 127 - 133 (1995)

Iodomethyllithium is shown to be an effective reagent for the one-carbon homologation of oxygenated boronic esters. The use of iodomethyllithium for the preparation of pinacol iodomethaneboronate and for the synthesis of epoxides from carbonyl compounds is also discussed.

Graphene oxide nanosheets supported manganese(III) porphyrin: a highly efficient and reusable biomimetic catalyst for epoxidation of alkenes with sodium periodate

Zarrinjahan, Alireza,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj

, p. 1509 - 1516 (2016)

Efficient epoxidation of alkenes catalyzed by tetrakis(p-aminophenyl)porphyrinatomanganese(III) chloride, [Mn(TNH2PP)Cl], supported on graphene oxide nanosheets, is reported. The catalyst, [Mn(TNH2PP)Cl]@GO, was prepared by covalent attachment of amino groups of porphyrin to carboxylic acid groups of GO. This new heterogenized catalyst was characterized by ICP, FT-IR and diffuse reflectance UV–vis spectroscopies, scanning electron microscopy and transmission electron microscopy. This catalyst was applied as an efficient and reusable catalyst in the epoxidation of alkenes with NaIO4 at room temperature, in the presence of imidazole as axial ligand. The most noteworthy advantage of [Mn(TNH2PP)Cl]@GO is its high reusability in the oxidation reactions, in which the catalyst was reused several times without significant loss of its catalytic activity.

Synthesis of a new schiff base oxovanadium complex with melamine and 2-hydroxynaphtaldehyde on modified magnetic nanoparticles as catalyst for allyl alcohols and olefins epoxidation

Farzaneh, Faezeh,Asgharpour, Zeinab

, (2019)

A new magnetically recoverable nanocatalyst designated as Fe3O4@SiO2@PTMS@Mel-Naph-VOcomplex was synthesize by covalent binding of a Schiff base ligand derived from melamine and 2-hydroxy1naphtaldehyde on the surface of silica coated iron oxide magnetic nanoparticles followed by complexation with VO (acac)2. Characterization of the prepared nanocatalyst was accomplished with FT-IR, XRD, SEM, HRTEM, VSM and atomic absorption techniques. It was found that the epoxidation of geraniol, trans-2-hexen-1-ol, 1-octen-3-ol, norbornene, and cyclooctene is highly selective, affording quantitative yields of the corresponding epoxides with tert-butyl hydroperoxide (TBHP) using Fe3O4@SiO2@Mel-Naph-VOcomplex as catalyst. High reaction yields, short reaction times, simple experimental and work up procedure, catalyst stability and excellent reusability even after five-cycles of usage in the case of geraniol are some advantages of this research.

Asymmetric epoxidation of unfunctionalized alkenes catalyzed by sugar moiety-modified chiral salen-Mn(III) complexes

Zhao, Jiquan,Zhang, Yuecheng,Han, Furong,Zhao, Shanshan

, p. 61 - 66 (2009)

Several chiral Schiff-base ligands with sugar moieties at C-3 (3′) or C-5 (5′) of salicylaldehyde were synthesized from reaction of salicylaldehyde derivatives with diamine. These ligands coordinated with Mn(III) to afford the corresponding chiral salen-M

Substituted perhydrofuropyrans: Easy preparation from 2-chloromethyl-3- (2-methoxyethoxy)propene through 3-methylene-1,6-diols

Lorenzo, Emilio,Alonso, Francisco,Yus, Miguel

, p. 1661 - 1665 (2000)

The reaction of 2-chloromethyl-3-(2-methoxyethoxy)prop-1-ene (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by treatment with an epoxide [E2=R3R4C(O)CHR5] at 0 to 20°C leads, after hydrolysis, to the expected unsaturated diols 2. When some compounds 2 (2e-h) are successively hydroborated (BH3 · THF) and oxidised (33% H2O2 and then PCC), the expected perhydrofuropyrans 3e-h are isolated directly. (C) 2000 Elsevier Science Ltd.

-

Hiyama et al.

, p. 1626 (1975)

-

Photoinduced electron-transfer oxidation of olefins with molecular oxygen sensitized by tetrasubstituted dimethoxybenzenes: A non-singlet-oxygen mechanism

Mori, Tadashi,Takamoto, Makolo,Wada, Takehiko,Inoue, Yoshihisa

, p. 2693 - 2707 (2001)

α-Methylstyrene (1) was photo-oxidized in the presence of a series of alkylated dimethoxybenzenes as sensitizers in an oxygen-saturated MeCN solution to afford the cleaved ketone 2, epoxide 3, as well as a small amount of the ene product 4 in ca. 1:1:0.04 ratio. The relative rate of conversion was well-correlated with the fluorescence quantum yield of sensitizers. Thus, a non-singlet-oxygen mechanism is proposed, in which an excited sensitizer is quenched by (ground-state) molecular oxygen to produce a sensitizer radical cation and a superoxide ion (O2-·), the former of which oxidizes the substrate, while the latter reacts with the resulting olefin radical cation (1-·) to give the major oxidation products. Photodurability of such electron-donating sensitizers is dramatically improved by substituting four aromatic H-atoms in 1,4-dimethoxybenzene with Me or fused alkyl groups, which provides us with an environmentally friendly, clean method of photochemical functionalization with molecular oxygen, alternative to the ene reaction via singlet oxygenation.

A novel strategy for clean and selective oxygenation of hydrocarbons with n-Bu4NHSO5 in neat water catalyzed by recyclable water-insoluble iron (III) tetraphenylporphyrins

Rezaeifard, Abdolreza,Jafarpour, Maasoumeh,Naeimi, Atena,Kaafi, Samira

, p. 761 - 765 (2011)

A novel heterogeneous method for efficient oxygenation of olefins to epoxides and saturated hydrocarbons to the related ketones using tetrabutylammonium peroxomonosulfate (n-Bu4NHSO5) in neat water catalyzed by Fe(TPP)Cl and Fe(TDCPP)Cl complexes as water-insoluble catalysts has been developed. The oxidation system proceeds well in the absence of organic co-solvents and surfactants. The electron-deficient Fe(TDCPP)Cl catalyst could easily be recycled and reused without loss of activity and the oxidant's by-product (n-Bu4NHSO4) could also be recycled.

Epoxidation of alkenes with NaIO4 catalyzed by an efficient and reusable natural polymer-supported ruthenium(III) salophen catalyst

Hatefi Ardakani,Moghadam,Saeednia,Pakdin-Parizi

, p. 631 - 636 (2016)

In the present study, preparation, characterization, and catalytic activity of Ru(salophen)Cl supported on chitosan were investigated. The prepared heterogeneous catalyst was characterized by diffuse reflectance UV-vis and FT-IR spectroscopic techniques, scanning electron microscopy, and neutron activation analysis. In this catalytic system, the effects of different solvents were studied in the epoxidation of cis-cyclooctene and CH3CN/H2O was found to be a better solvent. Also, the effects of oxygen donors such as NaIO4, H2O2, H2O2/urea(UHP), tert-BuOOH, NaClO, and Bu4NIO4 were studied in the epoxidation of cis-cyclooctene and NaIO4 was selected as an oxidant. The catalytic activity of this new heterogeneous catalyst in the epoxidation of cyclic and linear alkenes using NaIO4 as an oxidant in CH3CN/H2O at room temperature was studied. The obtained results led us to conclude that [Ru(salophen)Cl@ chitosan] is an efficient catalyst for the epoxidation of alkenes with NaIO4. The catalyst can be readily recovered simply by filtration and reused several times without any significant loss in its catalytic activity.

MoO2(acac)2 supported on multi-wall carbon nanotubes: Highly efficient and reusable catalysts for alkene epoxidation with tert-BuOOH

Esnaashari, Fariba,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Khosoropour, Ahmad Reza,Zakeri, Maryam,Hushmandrad, Shohreh

, p. 212 - 220 (2012)

In the present work, the preparation, characterization and investigation of the catalytic activity of MoO2(acac)2 supported on multi-wall carbon nanotubes modified with 2-aminopyridine and 1,2-diaminobenzene are reported. The catalysts were characterized by elemental analysis, FT-IR and UV-Vis spectroscopic techniques and scanning electron microscopy (SEM). The catalytic activity of molybdenyl acetylacetonate supported on multi-wall carbon nanotubes, MoO2(acac)@amine-MWCNTs, was investigated in the alkene epoxidation with tert-BuOOH. These heterogenized catalysts were successfully applied for efficient epoxidation of olefins with tert-BuOOH in 1,2-dichloroethane as the solvent. The prepared catalysts can be reused several times without significant loss of their catalytic activity.

-

Niki,Kamiya

, p. 583,584 (1967)

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Manganese(II) complexes of hydrazone based NNO-donor ligands and their catalytic activity in the oxidation of olefins

Bikas, Rahman,Ghorbanloo, Massomeh,Sasani, Roya,Pantenburg, Ingo,Meyer, Gerd

, p. 819 - 830 (2017)

The reaction between tridentate NNO donor hydrazone ligands, (E)-2-cyano-N′-(phenyl(pyridin-2-yl)methylene)acetohydrazide (HL1) and (E)-2-cyano-N′-(1-(pyridin-2-yl)ethylidene)acetohydrazide (HL2), with MnCl2·4H2O in methanol resulted in [Mn(HL1)Cl2(CH3OH)] (1) and [Mn(HL2)Cl2(CH3OH)] (2). Molecular structures of the complexes were determined by single-crystal X-ray diffraction. All of the investigated compounds were further characterized by elemental analysis, FT-IR, TGA, and UV–Vis spectroscopy. These complexes were used as catalysts for olefin oxidation in the presence of tert-butylhydroperoxide (TBHP) as an oxidant. Under similar experimental conditions with equal manganese loading, the presence of [Mn(HL2)Cl2(CH3OH)] (2) resulted in higher conversion than [Mn(HL1)Cl2(CH3OH)] (1).

Catalytic activity of carbon nanotube supported iron(III) and manganese(III) porphyrins in oxidation of olefins with tert-butyl hydroperoxide: Higher activity of the iron(III) porphyrin

Rayati, Saeed,Jafarzadeh, Parisa,Zakavi, Saeed

, p. 40 - 44 (2013)

Oxidation of olefins with tert-butyl hydroperoxide (TBHP) catalyzed by carbon nanotube supported iron(III) and manganese(III) complexes of meso-tetrakis(4-hydroxyphenyl)porphyrin is reported. The results show higher catalytic activity of the Fe(III) complex compared to the Mn(III) one. With the exception of cyclooctene which gives cyclooctene oxide as the sole product, oxidation of styrene, α-methyl styrene and cyclohexene leads to the formation of benzaldehyde, acetophenone and cyclohexene-1-one as the major product, respectively. In this study, acetonitrile has been found to be the best solvent for reaction performed in the presence of the manganese and iron porphyrin. In comparison of the two metalloporphyrins, catalytic activity of the manganese porphyrin is more sensitive to the type of solvent than the iron one. In spite of the crucial role of imidazole (ImH) on catalytic performance of the manganese porphyrin, the presence of ImH has a negative effect on the activity of the iron porphyrin. The nano-tube supported iron porphyrin may be recovered and reused at least four times without significant loss of the catalytic activity.

-

Farrall et al.

, p. 203 (1979)

-

Nickel complexes with N2O donor ligands: Syntheses, structures, catalysis and magnetic studies

Chakraborty, Jishnunil,Nandi, Mahasweta,Mayer-Figge, Heike,Sheldrick, William S.,Sorace, Lorenzo,Bhaumik, Asim,Banerjee, Pradyot

, p. 5033 - 5044 (2007)

Two new terephthalato-bridged tetranuclear polymeric NiII complexes, namely [Ni4L41(μ-tp- κ4-O)(H2O)2(μ-tp-κ2- O)]· 2C2H5OH·CH3OH·3H 2O (1) and [Ni4L42(μ-tp- κ4-O)(H2O)2(μ-tp-κ2- O)]·3H2O (2) [L1 = N-(3-aminopropyl)-5- bromosalicylaldimine and L2 = N-(3-aminopropyl)salicylaldimine], are reported along with the syntheses and structures of the dicyanoargentate-bridged polymeric complexes [Ni(L1)(H2O)-{Ag(CN) 2}]α (3) and [Ni(L3)(MeOH){Ag(CN) 2}]α (4) [L3 = N-(3-amino-2,2-dimethylpropyl)-5- bromosalicylaldimine]. All four complexes are found to be effective heterogeneous catalysts for the epoxidation of alkenes such as styrene, α-methylstyrene and cyclohexene in the presence of tert-butyl hydroperoxide. The variable-temperature magnetic susceptibility measurements (300-2 K) of complex 1 show a fair degree of antiferromagnetic coupling between the NiII centers. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Chiral porous poly(ionic liquid)s: Facile one-pot, one-step synthesis and efficient heterogeneous catalysts for asymmetric epoxidation of olefins

Tian, Yabing,Wang, Jixia,Zhang, Shiguo,Zhang, Yan

, (2022/01/26)

Ionic liquids are potential media/solvents for asymmetric synthesis when combined with chiral catalysts, while most reported catalysts are homogenous, making them difficult to separate from the reaction systems. Herein, chiral porous poly(ionic liquid)s (

AuCu/ZnO heterogeneous photocatalysts: Photodeposited AuCu alloy effect on product selectivity in alkene epoxidation

Brock, Aidan J.,Deshan, Athukoralalage Don K.,Sarina, Sarina,Waclawik, Eric R.,Weerathunga, Helapiyumi,Zhu, Huai-Yong

, (2021/12/24)

AuCu metal alloy nanoparticles were photodeposited on ZnO nanorods (ZnO_NRs) which proved to be effective photocatalysts for alkene epoxidation. The alloy nanoparticles were photodeposited onto ZnO nanorods with controlled ratios of gold and copper, with the deposition monitored in situ by UV-Vis spectroscopy. The alloy catalyst hybrids were tested for activity toward styrene epoxidation and HMF oxidative esterification, where the photoreactions were both optimized for time, temperature, and metal ratio content of the catalyst. The Au0.54Cu1/ZnO_NR alloy catalysts showed excellent photocatalytic activity and were most effective for conversion of styrene to styrene epoxide, where the product selectivity could be controlled by varying the metal ratio. Cu content in the alloy NP was essential to this process, as shown by the extrema in terms of metal content, using Au/ZnO only, where 100% benzaldehyde was obtained as the product. Au/ZnO evidenced best photocatalytic activity for HMF esterification, with conversion rapidly diminishing upon alloying of Au with Cu. A detailed XPS study was carried out to investigate reaction mechanism based on these studies, in particular, mechanisms are proposed for styrene epoxidation and oxidation cycles using the AuCu/ZnO_NR photocatalysts.

Construction of an Asymmetric Porphyrinic Zirconium Metal-Organic Framework through Ionic Postchiral Modification

Berijani, Kayhaneh,Morsali, Ali

, p. 206 - 218 (2021/01/11)

Herein, one kind of neutral chiral zirconium metal-organic framework (Zr-MOF) was reported from the porphyrinic MOF (PMOF) family with a metallolinker (MnIII-porphyrin) as the achiral polytopic linker [free base tetrakis(4-carboxyphenyl)porphyrin] and chiral anions. Achiral Zr-MOF was chiralized through the exchange of primitive anions with new chiral organic anions (postsynthetic exchange). This chiral functional porphyrinic MOF (CPMOF) was characterized by several techniques such as powder X-ray diffraction, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, 1H NMR, energy-dispersive X-ray spectroscopy, scanning electron microscopy, and Brunauer-Emmett-Teller measurements. In the resulting structure, there are two active metal sites as Lewis acid centers (Zr and Mn) and chiral species as Br?nsted acid sites along with their cooperation as nucleophiles. This CPMOF shows considerable bimodal porosity with high surface area and stability. Additionally, its ability was investigated in asymmetric catalyses of prochiral substrates. Interactions between framework chiral species and prochiral substrates have large impacts on the catalytic ability and chirality induction. This chiral catalyst proceeded asymmetric epoxidation and CO2 fixation reactions at lower pressure with high enantioselectivity due to Lewis acids and chiral auxiliary nucleophiles without significant loss of activity up to the sixth step of consecutive cycles of reusability. Observations revealed that chiralization of Zr-MOF could happen by a succinct strategy that can be a convenient method to design chiral MOFs.

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

Franssen, Maurice C. R.,Hollmann, Frank,Martínez-Montero, Lía,Paul, Caroline E.,Süss, Philipp,Schallmey, Anett,Tischler, Dirk

, p. 5077 - 5085 (2021/08/16)

Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction

Malunavar, Shruti S.,Sutar, Suraj M.,Prabhala, Pavankumar,Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Aridoss, Gopalakrishnan,Laali, Kenneth K.

supporting information, (2021/09/13)

The potential of [PAIM][NTf2]/BMIM-ILs as a base/solvent in the Corey-Chaykovsky reaction is demonstrated by the facile synthesis of libraries of functionalized cyclopropanes from enones and oxiranes from aldehydes and ketones, at room temperature in respectable isolated yields. To demonstrate their application, the synthesized epoxides were employed as substrates for the synthesis of a library of 2,3-disubstituted quinolines, using [BMIM(SO3H)][OTf]/[BMIM][PF6] as a catalyst/solvent. The potential for recycling/reuse of the IL solvents was also explored.

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
With tert.-butylhydroperoxide; cobalt(III) oxide; In N,N-dimethyl-formamide; at 69.84 ℃; for 5h; Sonication; Molecular sieve;
(R)-2-methyl-2-phenyloxirane
2085-88-3,2404-43-5,21019-52-3,100018-61-9

(R)-2-methyl-2-phenyloxirane

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With iron oxide; oxygen; isobutyraldehyde; In acetonitrile; at 25 ℃; for 8h; under 750.075 Torr;
8 %Chromat.
20 %Chromat.
2-methyl-2-phenyloxirane
2085-88-3

2-methyl-2-phenyloxirane

benzaldehyde
100-52-7

benzaldehyde

acetophenone
98-86-2

acetophenone

Conditions
Conditions Yield
With oxygen; isobutyraldehyde; In acetonitrile; at 60 ℃; for 2h;
(R)-2-methyl-2-phenyloxirane
2085-88-3,2404-43-5,21019-52-3,100018-61-9

(R)-2-methyl-2-phenyloxirane

benzaldehyde
100-52-7

benzaldehyde

(2S)-2-methyl-2-phenyloxirane
2404-43-5

(2S)-2-methyl-2-phenyloxirane

Conditions
Conditions Yield
With oxygen; isobutyraldehyde; In acetonitrile; at 45 ℃; for 8h; Reagent/catalyst; enantioselective reaction;
77%
8%
15%
With oxygen; isobutyraldehyde; In acetonitrile; at 40 ℃; for 2h; under 750.075 Torr; enantioselective reaction;
35 %Chromat.
30 %Chromat.
35 %Chromat.
With oxygen; isobutyraldehyde; In acetonitrile; at 45 ℃; for 4h; enantioselective reaction; Catalytic behavior;
74 % ee
Benzoylformic acid
611-73-4

Benzoylformic acid

2-methyl-2-phenyloxirane
2085-88-3

2-methyl-2-phenyloxirane

benzoic acid phenyl ester
93-99-2

benzoic acid phenyl ester

benzaldehyde
100-52-7

benzaldehyde

acetophenone
98-86-2

acetophenone

Conditions
Conditions Yield
With pyridine; oxygen; isopropenylbenzene; In benzene; at 20 ℃; Further byproducts given; Irradiation;
16 % Chromat.
53 % Chromat.
14 % Chromat.
30 % Chromat.
2-methyl-2-phenyloxirane
2085-88-3

2-methyl-2-phenyloxirane

benzoic acid phenyl ester
93-99-2

benzoic acid phenyl ester

benzaldehyde
100-52-7

benzaldehyde

acetophenone
98-86-2

acetophenone

Conditions
Conditions Yield
With pyridine; oxygen; Benzoylformic acid; In benzene; at 20 ℃; Yield given. Further byproducts given. Yields of byproduct given; Irradiation;
2-methyl-2-phenyloxirane
2085-88-3

2-methyl-2-phenyloxirane

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With dihydrogen peroxide; In water; acetonitrile; at 50 ℃; for 2h;
2-methyl-2-phenyloxirane
2085-88-3

2-methyl-2-phenyloxirane

benzaldehyde
100-52-7

benzaldehyde

1-phenyl-acetone
103-79-7,136675-26-8

1-phenyl-acetone

Conditions
Conditions Yield
With phosphomolybdic acid; dihydrogen peroxide; In water; acetonitrile; at 50 ℃; for 2h;
2-methyl-2-phenyloxirane
2085-88-3

2-methyl-2-phenyloxirane

hydratropic acid
492-37-5,2328-24-7

hydratropic acid

2-Phenylpropanal
34713-70-7

2-Phenylpropanal

1,2-dihydroxy-2-phenylpropane
4217-66-7

1,2-dihydroxy-2-phenylpropane

acetophenone
98-86-2

acetophenone

Conditions
Conditions Yield
With dihydrogen peroxide; H-mordenite; In acetonitrile; at 79.9 ℃; Product distribution; var. zeolites and temp.; other alkenes;
norborn-2-ene
498-66-8

norborn-2-ene

2,3-epoxynorbornane
278-74-0

2,3-epoxynorbornane

2-methyl-2-phenyloxirane
2085-88-3

2-methyl-2-phenyloxirane

Conditions
Conditions Yield
With hydroxo(5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato)iron(III); 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 3h; competitive epoxidation in the presence of var. iron porphyrins; other alkenes, other oxidants, other catalyst, other solvents;

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