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Cas Database

123-11-5

123-11-5

Identification

  • Product Name:p-Anisaldehyde

  • CAS Number: 123-11-5

  • EINECS:204-602-6

  • Molecular Weight:136.15

  • Molecular Formula: C8H8O2

  • HS Code:29124900

  • Mol File:123-11-5.mol

Synonyms:p-Formylanisole;p-Methoxybenzaldehyde;4-Anisaldehyde;4-Methoxybenzaldehyde;Anisaldehyde;Anisic aldehyde;Aubepine;Crategine;NSC 5590;Obepin;p-Anisic aldehyde;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn,Xi,T,F

  • Signal Word:No signal word.

  • Hazard Statement:none

  • 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:Usbiological
  • Product Description:p-Anisaldehyde
  • Packaging:100mg
  • Price:$ 255
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  • Manufacture/Brand:TRC
  • Product Description:Anisaldehyde
  • Packaging:50g
  • Price:$ 135
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  • Manufacture/Brand:TRC
  • Product Description:Anisaldehyde
  • Packaging:100g
  • Price:$ 215
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  • Manufacture/Brand:TCI Chemical
  • Product Description:p-Anisaldehyde >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:p-Anisaldehyde (contains Acetic Acid, H2SO4)Ethanol Solution[for TLC Stain]
  • Packaging:500mL
  • Price:$ 114
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  • Manufacture/Brand:TCI Chemical
  • Product Description:p-Anisaldehyde (contains Acetic Acid, H2SO4)Ethanol Solution[for TLC Stain]
  • Packaging:100mL
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  • Manufacture/Brand:TCI Chemical
  • Product Description:p-Anisaldehyde >99.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:p-Anisaldehyde natural, FG
  • Packaging:1 kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:p-Anisaldehyde natural, 98%, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:p-Anisaldehyde ≥97.5%, FCC, FG
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Relevant articles and documentsAll total 1753 Articles be found

CuII-salan compounds: Synthesis, characterization and evaluation of their potential as oxidation catalysts

Ad?o, Pedro,Barroso, Sónia,Avecilla, Fernando,Oliveira, M. Concei??o,Pessoa, Jo?o Costa

, p. 212 - 223 (2014)

We report the synthesis and characterization of several salan-type Cu II complexes. Suitable crystals suitable for X-ray diffraction were obtained for several of the CuII complexes, including a half-salen compound, revealing square-planar coordination environments common to d9 species. The CuII-salan complexes are tested as catalysts in sulfoxidation, alkene oxidation, and oxidative naphthol coupling. At room temperature the compounds exhibit low to moderate catalytic activity in sulfoxidations and alkene oxidations, but no activity in oxidative naphthol coupling. The saturated coordination environments around the Cu centers probably are the main reason for the lower catalytic activities compared to the Ti- and V-salan analogs. Spectroscopic and mass spectrometry studies revealed that the CuII-salan complexes decompose, in the presence of H2O2, significantly faster at 40 °C than at room temperature. The catalytic activity observed is probably due to the CuII-salan degradation products, observed in the mass spectrometry studies, and not to the original CuII-salan precursors.

Syntheses of U3O8 nanoparticles form four different uranyl complexes: Their catalytic performance for various alcohol oxidations

Majumder, Ishani,Chatterjee, Sourav,Fischer, Roland C.,Neogi, Swarup Kumar,Mautner, Franz A.,Chattopadhyay, Tanmay

, p. 112 - 122 (2017)

Two dinuclear complexes namely [(UO2)2(L1)2(DMSO)2] (1) and [(UO2)2(L2)2(DMSO)2] (2) of two Schiff base ligands 2-[(2-hydroxy-3-methoxy-benzylidene)-amino]-2-hydroxymethyl propane-1,3-diol (HL1) and 2-[(3,5-dichloro-2-hydroxy-benzylidene)-amino]-2-hydroxymethyl-propane-1,3-diol (HL2) obtained by condensation of the aldehydes 2-hydroxy-3-methoxy-benzaldehyde and 3, 5-dichloro salicylaldehyde with tris(hydroxymethyl)aminomethane ammine, have been synthesized. On the other hand, when the two aldehydes were treated with uranyl nitrate two mononuclear complexes, [(UO2)(L3)2(DMSO)2] (3) and [(UO2)(L4)2(DMSO)2] (4), are obtained. The complexes are then heated at 800?°C in open atmosphere to obtain the U3O8 nanomaterials as the final product. X-ray diffraction (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) were employed to characterize the so obtained the U3O8 nanoparticles. Studies shows the synthesized U3O8 nanoparticles obtained from different complexes were different as far as morphology and size are concerned. All four different U3O8 nanoparticles explored as oxidising catalyst to oxidize alcohols where morphology of the nanoparticles controls the catalytic efficiency.

One-pot synthesis of silica gel confined functional ionic liquids: Effective catalysts for deoximation under mild conditions

Li, Dongmei,Shi, Feng,Guo, Shu,Deng, Youquan

, p. 265 - 268 (2004)

Several acid-functional ionic liquids were physically confined into the silica gel through a sol-gel process and used as effective catalysts for deoximation reactions, which proceeded under ambient temperatures without addition of any co-catalysts or oxidizing and reducing agents.

Synthesis and biological activity of hydroxylated analogs of RCAI-80

Shiozaki, Masao,Tashiro, Takuya,Koshino, Hiroyuki,Shigeura, Tomokuni,Watarai, Hiroshi,Taniguchi, Masaru,Mori, Kenji

, p. 9710 - 9725 (2013)

RCAI-80 is one of the ester analogs of KRN7000 (α-galactosylceramide) . This compound released mainly T helper 2 (Th2) cytokines, such as IL-4 rather than T helper 1 (Th1) cytokines, such as IFNγ from the invariant natural killer T (iNKT) cells. In addition, it has been known that some of the hydroxylated derivatives of KRN7000 make the cytokine secretion bias to Th2 by decreasing the IFNγ production to almost zero. This time, the three compounds having these two characteristic properties, namely an ester group and also some extra hydroxy groups existing on the ester side chain and/or on the 2-acyloxy-3,4-dihydroxyoctadecyl main chain of RCAI-80, were synthesized to examine the biological activities. As a result, it was found that these compounds made the cytokine secretion skew to Th2. Therefore, their effectiveness for experimental autoimmune encephalomyelitis (EAE) was examined. It was recognized that one of them showed moderate suppression of EAE symptom.

Nanostructured rutile TiO2 for selective photocatalytic oxidation of aromatic alcohols to aldehydes in water

Yurdakal, Sedat,Palmisano, Giovanni,Loddo, Vittorio,Augugliaro, Vincenzo,Palmisano, Leonardo

, p. 1568 - 1569 (2008)

Selective photocatalytic oxidation of aromatic alcohols to aldehydes was performed in water in the presence of TiO2 rutile photocatalysts that exhibited a low degree of crystallinity. The nanostructured rutile samples, prepared ex TiCl4 at very low temperature, ensured a selectivity toward the aldehyde 3 to 4-fold higher than the commercial rutile tested (Sigma-Aldrich). Copyright

Synthesis, characterization and catalytic activity of new Cr(III) complex in oxidation of primary alcohols to aldehydes

Noshiranzadeh, Nader,Bikas, Rahman,?lepokura, Katarzyna,Mayeli, Mina,Lis, Tadeusz

, p. 176 - 182 (2014)

New mononuclear complex of chromium(III), [Cr(bp)(N3)(CH 3OH)]·2CH3OH has been synthesized where H 2bp is N,N-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-N',N'- dimethylethylene-1,2-diamine. The complex was character

Gold nanoparticle-modified TiO2/SBA-15 nanocomposites as active plasmonic photocatalysts for the selective oxidation of aromatic alcohols

Chen, Yu,Li, Weizun,Wang, Jingyu,Yang, Qian,Hou, Qidong,Ju, Meiting

, p. 70352 - 70363 (2016)

The catalytic performance of noble-metal on mesoporous silica hosts has been widely investigated because the effects of surface plasmon resonance can open new avenues for the improvement of catalytic performance under light irradiation. In this study, a s

A ceric ammonium nitrate based oxidative cleavage pathway for the asymmetric aldol adducts of oxadiazinones derived from (1R,2S)-N-p-methoxybenzylnorephedrine

Leise, Austin R.,Comas, Nicole,Harrison, Doug,Patel, Dipak,Whitemiller, Eileen G.,Wilson, Jennifer,Timms, Jacob,Golightly, Ian,Hamaker, Christopher G.,Hitchcock, Shawn R.

, p. 1154 - 1162 (2017)

An N4-p-methoxybenzyloxadiazinone has been prepared from (1R,2S)-norephedrine through a process of reductive amination, N-nitrosation, reduction, and cyclization. The oxadiazinone was acylated and employed in the asymmetric aldol addition reaction with aromatic and aliphatic aldehydes to yield aldol adducts in isolated yields ranging from 54% to 90%. Selected aldol adducts were treated with ceric ammonium nitrate in aqueous acetonitrile to afford the desired β-hydroxycarboxylic acids through a tandem process of oxidative cleavage of the N4-p-methoxybenzyl group and acidic hydrolysis of the N3-acyl side chain. The β-hydroxycarboxylic acids were recovered in high diastereomeric purity as determined by 500 MHz 1H NMR spectroscopy and the absolute configuration was confirmed by polarimetry. The chiral auxiliary unit, the 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone), was converted into its corresponding 3,6-dihydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone) through an oxidative pathway promoted by the ceric ammonium nitrate.

Lewis acid-catalyzed reactions of ethyl diazoacetate with aldehydes. Synthesis of α-formyl esters by a sequence of aldol reaction and 1,2- nucleophilic rearrangement

Kanemasa, Shuji,Kanai, Toshio,Araki, Takahiro,Wada, Eiji

, p. 5055 - 5058 (1999)

Ethyl diazoacetate reacts with a variety of aldehydes in the presence of a Lewis acid catalyst to give either β-keto esters or α-formyl esters, the types of products mainly depending upon the nature of Lewis acid catalysts employed. Reactions catalyzed by Lewis acids such as SnCl2 and SnCl4 provide β-keto esters via nucleophilic 1,2-hydride migration, while those catalyzed by trimethylsilyl triflate give α-formyl esters via migration of the substituent of the aldehyde. Reaction mechanisms are discussed.

New oligostilbenes having a benzofuran from Vitis vinifera 'Kyohou'

Ito, Junko,Takaya, Yoshiaki,Oshima, Yoshiteru,Niwa, Masatake

, p. 2529 - 2544 (1999)

Three new oligostilbenes having a benzofuran moiety, viniferifuran, (+)- vitisifuran A and (-)-vitisifuran B, were isolated from Vitis vinifera 'Kyohou'. The structures of these oligostilbenes including the absolute configuration were elucidated by spectroscopic and chemical methods. Furthermore, these were chemically transformed from (+)-ε-viniferin, (+)- vitisin A and (-)-vitisin B, respectively, whose absolute configurations are known.

Scholl,Hilgers

, p. 648 (1903)

9,10-Dicyanoanthracene-sensitized Photo-oxygenation of trans-1,2-Di(carbazol-9-yl)cyclobutane via Electron-transfer

Mizuno, Kazuhiko,Murakami, Kazuhiro,Kamiyama, Nobuhiro,Otsuji, Yoshio

, p. 462 - 463 (1983)

9,10-Dicyanoanthracene-sensitized photo-oxygenation of trans-1,2-di(carbazol-9-yl)cyclobutane in acetonitrile efficiently affords 3,6-di(carbazol-9-yl)-1,2-dioxan.

Facile one-pot synthesis of anisaldehyde

Yu, Jing,Shen, Minmin,Deng, Lianli,Gan, Lu,Ha, Chengyong

, p. 541 - 543 (2012)

At room temperature, anisaldehyde (4-methoxybenzaldehyde) is synthesized based on the ozonolysis of anethole (1-methoxy-4-(1-propenyl)-benzene) in a novel and environmentally friendly system composed of water and ethyl acetate. In the presence of water, ozonolysis of anethole results in the direct formation of anisaldehyde, avoiding the isolation or decomposition of ozonide.

A biomimetic approach to the synthesis of rocaglamide based on a photochemical [2 + 2] cycloaddition of a cinnamate unit to a flavone

Hailes,Raphael,Staunton

, p. 5313 - 5316 (1993)

In attempting a biomimetic synthesis of rocaglamide, we have discovered the first examples of photochemically induced cycloaddition reactions involving a flavone system.

-

Mandell et al.

, p. 1461 (1977)

-

A DyP-type peroxidase of pleurotus sapidus with alkene cleaving activity

Berger, Ralf G.,Ersoy, Franziska,Krahe, Nina-Katharina

, (2020)

Alkene cleavage is a possibility to generate aldehydes with olfactory properties for the fragrance and flavor industry. A dye-decolorizing peroxidase (DyP) of the basidiomycete Pleurotus sapidus (PsaPOX) cleaved the aryl alkene trans-anethole. The PsaPOX was semi-purified from the mycelium via FPLC, and the corresponding gene was identified. The amino acid sequence as well as the predicted tertiary structure showed typical characteristics of DyPs as well as a non-canonical Mn2+-oxidation site on its surface. The gene was expressed in Komagataella pfaffii GS115 yielding activities up to 142 U/L using 2,20-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) as substrate. PsaPOX exhibited optima at pH 3.5 and 40 ?C and showed highest peroxidase activity in the presence of 100 μM H2O2 and 25 mM Mn2+. PsaPOX lacked the typical activity of DyPs towards anthraquinone dyes, but oxidized Mn2+ to Mn3+. In addition, bleaching of β-carotene and annatto was observed. Biotransformation experiments verified the alkene cleavage activity towards the aryl alkenes (E)-methyl isoeugenol, α-methylstyrene, and trans-anethole, which was increased almost twofold in the presence of Mn2+. The resultant aldehydes are olfactants used in the fragrance and flavor industry. PsaPOX is the first described DyP with alkene cleavage activity towards aryl alkenes and showed potential as biocatalyst for flavor production.

-

Rakoutz et al.

, p. 3723 (1978)

-

Alkene cleavage by white-rot Trametes hirsuta: Inducing enzyme activity by a fungicide

Rajagopalan, Aashrita,Seisser, Birgit,Mutti, Francesco G.,Schober, Markus,Kroutil, Wolfgang

, p. 118 - 122 (2013)

Alkene cleavage is a widely employed oxidation reaction in organic chemistry. An enzyme preparation of the wood degrading fungus Trametes hirsuta is known to cleave the CC double bond adjacent to an aromatic ring to give the corresponding carbonyl compound at the expense of molecular oxygen as the sole oxidant. Lab-grown fungus cultures displayed varied activity and lost their alkene cleavage activity over generations of growth. t-Anethole, which is the best accepted substrate by the enzyme, is described as a major component of essential oils produced by certain plants with powerful fungicidal property. We could now show that the alkene cleaving activity was improved by the addition of the fungicide t-anethole during culture growth which represented to be an efficient method to produce cells possessing a consistent level of high alkene cleavage activity.

Aminolysis of 6-[1-(2,6-difluorophenyl)cyclopropyl]-5-methyl-2-(nitroamino)pyrimidin-4(3H)-one

Novakov,Brunilina,Vernigora,Kirillov,Mkrtchyan,Navrotskii,Sheikin,Yablokov,Ruchko,Kachala

, p. 1844 - 1850 (2017)

The aminolysis of 6-[1-(2,6-difluorophenyl)cyclopropyl]-5-methyl-2-(nitroamino)pyrimidin-4(3H)-one with various amines in butan-1-ol and under solvent-free conditions is successful when the amino group in the reagent is sterically unshielded and the reaction medium is characterized by a high dielectric permittivity. Reactions of the title compound with sterically shielded amines are accompanied by alcoholysis where the amine acts as a base catalyst.

Rate and equilibrium constants for hydrolysis and isomerization of (E)- and (Z)-p-methoxybenzaldehyde oximes

O'Ferrall, Rory A. More,O'Brien, Deirdre

, p. 631 - 640 (2004)

The interconversion and hydrolysis of (E)- and (Z)-oximes of p-methoxybenzaldehyde in aqueous solutions of perchloric acid have been studied in the acid concentration range from pH 3 to UM. Kinetic measurements confirm that isomerization and hydrolysis proceed through a common tetrahedral intermediate TQ. At low acid concentrations, attack of water on the protonated oxime is rate-determining in the hydrolysis reaction and no separate isomerization is observable. However, as the acid concentration increases the attack of water becomes faster than loss hydroxylamine from T0 and E to Z isomerization is observable as a faster reaction in competition with hydrolysis. From kinetic and equilibrium measurements a comprehensive set of rate and equilibrium constants for protonation, hydrolysis and hydration of (E)- and (Z)-oximes is derived. For the neutral oximes KT = [E]/[Z] = 8 and for the protonated oximes pKa = -0.55 and 0.80 for the E and Z isomers, respectively. By combining these values with measurements of oxime formation from p-methoxybenzaldehyde and hydroxylamine, including Kadd = [T0]/ [aldehyde][NH2OH] = [T2]/[oxime] = 1.8, values of pKR = -3.65 and -5.90 and KH2O = 6.3 × 10-5 and 7.9 × 10-6 for (Z)- and (Z)-oximes may also be derived. The values of pKa, pKR and KH2O for the oximes are compared with corresponding values for p-methoxybenzaldehyde and its hydrate (≡T0). Copyright 2004 John Wiley & Sons, Ltd. Additional material for this paper is available in Wiley Interscience.

Demonstration of the chemical competence of an iminodiazonium ion to serve as the reactive intermediate of a schmidt reaction

Richard, John P.,Amyes, Tina L.,Lee, Yong-Gu,Jagannadham, Vandanapu

, p. 10833 - 10834 (1994)

-

Hydrogen evolution using the visible-light-induced metal-to-polyoxometalate multiple electron transfer

Suzuki, Kosuke,Tang, Fei,Kikukawa, Yuji,Yamaguchi, Kazuya,Mizuno, Noritaka

, p. 1429 - 1431 (2014)

A tetranuclear cerium-containing polyoxometalate, TBA6-[{Ce(H2O)}2{Ce(CH3CN)}2(μ4-O)(γ-SiW10O36)2] (I, TBA: tetra-n-butylammonium), showed a unique intramolecular multiple electron transfer (Ce3+-to-POM(W6+)) on irradiation of visible light (λ > 400 nm). This could induce hydrogen (H2) evolution using alcohols as the electron donors, and a high turnover number (TON) of 1960 was achieved. Moreover, I could be reused without an appreciable loss in its catalytic performance.

Copper-Catalyzed Cleavage of Unstrained C-C Bonds for the Synthesis of 1-Acyloxy-2,2,6,6-tetramethylpiperidines from Cyclic or Acyclic Ketones

Jiang, Qijian,Yang, Luo,Zhou, Wang

, p. 2163 - 2168 (2017)

A copper-catalyzed approach for the synthesis of 1-acyloxy-2,2,6,6-tetramethylpiperidines through the C-C bond cleavage of cyclic or acyclic ketones was developed. In this chemistry, a combination of CuCl 2 ·2H 2 O, 1,10-phenanthroline monohydrate, and aniline was crucial for the formation of the desired products by the reaction of ketones with TEMPO. This research provides a new strategy for the further transformation of α-aryl cyclic or acyclic ketones.

Nitrogen dioxide-catalyzed aerobic oxidation of benzyl alcohols under cocatalyst and acid-free conditions

Ren, Fangping,Tian, Xinzhe,Ren, Yun-Lai,Zhao, Shuang,Wang, Jianji,Zhao, Bo

, p. 98 - 101 (2017)

Nitrogen dioxide is usually considered as a mediator between dioxygen and the catalysts for the aerobic oxidation of alcohols. Here, we report that nitrogen dioxide has an ability to catalyze this reaction, which not only avoids the use of the cocatalysts or the acids in traditional approaches, but also reveals a method for the present transformation with a single component catalyst. A series of primary and secondary benzyl alcohols underwent this transformation to give the targeted products in low to high yields.

Zeolite-supported chromium(VI) oxide: A mild, efficient, and inexpensive reagent for oxidative deprotection of trimethylsilyl ethers under microwave irradiation

Heravi, Majid M.,Hydarzadeh, Fereshteh,Farhangi, Yahya,Ghassemzadeh, Mitra

, p. 1473 - 1475 (2004)

Primary and secondary trimethylsilyl ethers are efficiently converted, to the corresponding carbonyl compounds using HZSM-5 zeolite-supported CrO 3 under microwave irradiation in solventless system.

Synthesis of a stereoisomer of wortmannilactone C - failure and success

Dittoo, Aurélia,Brandt, Damien,Bellosta, Véronique,Cossy, Janine

, p. 5835 - 5848 (2015)

Abstract A diastereomer of wortmannilactone C was synthesized according to a versatile strategy from tert-butyl 3-hydroxypropanoate and ethyl (R)-3-hydroxybutanoate, by using versatile organometallic reagents to control four stereogenic centers out of five. The successful strategy consists of the construction of the C13-C17 triene by using a Liebeskind coupling and the construction of the C2-C7 triene by utilizing a Horner-Wadsworth-Emmons reaction to form the macrocycle.

Synthesis of α-CF3 ketones from alkenes and electrophilic trifluoromethylating reagents by visible-light driven photoredox catalysis

Li, Lun,Chen, Qing-Yun,Guo, Yong

, p. 79 - 83 (2014)

α-Trifluoromethyl ketones are important fluorinated intermediates and products in chemical synthesis and medicinal development. Herein, visible light-catalyzed photoredox trifluoromethylation of 1-aryl-2-alkyl substituted alkenes using an electrophilic tr

Copper(II) catalyzed selective oxidation of primary alcohols to aldehydes with atmospheric oxygen

Velusamy, Subbarayan,Srinivasan, Arumugam,Punniyamurthy

, p. 923 - 926 (2006)

Copper(II) complex 1 selectively catalyzes the oxidation of primary alcohols to aldehydes in high yields by atmospheric oxygen in the presence of TEMPO. This procedure does not require an additive and the catalyst 1 is recyclable without loss of activity.

The oxidation of sulfides by chromium(V)

Lepage, Carmela R. Jackson,Mihichuk, Lynn,Lee, Donald G.

, p. 75 - 80 (2003)

The mechanism for the oxidation of sulfides by [(me4-salen)CrV(O)(pyO)]CF3SO3, where me4-salen is 8,8,8',8'-tetramethylsalen and pyO is pyridine N-oxide, has been investigated. Results from Hammett correlations on the rates of oxidation of substituted thioanisoles, frontier molecular orbital calculations, and product studies are consistent with a mechanism that is initiated by a single electron transfer to give a radical cation intermediate.

The activation of C-H bonds using an EmimAc/MWCNTs composite: A comparison of the composite used as electrolyte and electrode in aqueous media

Zhu, Yinghong,Chen, Ziying,Zhang, Jianqing,Wu, Qianqian,Ma, Chun'An,Little, R. Daniel

, p. 308 - 312 (2016)

An EmimAc/MWCNTs composite was prepared and characterized through SEM and TEM. The MWCNTs were well dispersed after combining with alkaline EmimAc. The activity of the composite was demonstrated by CV and controlled potential electrolysis. The composite could be used independently as electrolyte or electrode and showed excellent activity toward the electro-oxidation of the C-H bond of benzylic systems, and did so at a lower oxidation potential than when using EmimAc or MWCNTs. After modification, the pH value of the composite was adjusted to the acid range, and the yield of aldehyde adducts obtained through electro-oxidation improved.

Detailed Mechanistic Study of the Non-enzymatic Formation of the Discoipyrrole Family of Natural Products

Colosimo, Dominic A.,Macmillan, John B.

, p. 2383 - 2388 (2016)

Discoipyrroles A-D (DPA-DPD) are recently discovered natural products produced by the marine bacterium Bacillus hunanensis that exhibit anticancer properties in vitro. Initial biosynthetic studies demonstrated that DPA is formed in the liquid fermentation medium of B. hunanensis from three secreted metabolites through an unknown but protein-independent mechanism. The increased identification of natural products that depend on non-enzymatic steps creates a significant need to understand how these different reactions can occur. In this work, we utilized 15N-labeled starting materials and continuous high-sensitivity 1H-15N HMBC NMR spectroscopy to resolve scarce reaction intermediates of the non-enzymatic discoipyrrole reaction as they formed in real time. This information guided supplemental experiments using 13C- and 18O-labeled materials to elucidate the details of DPA's non-enzymatic biosynthesis, which features a highly concerted pyrrole formation and necessary O2-mediated oxidation. We have illustrated a novel way of using isotopically enhanced two-dimensional NMR spectroscopy to interrogate reaction mechanisms as they occur. In addition, these findings add to our growing knowledge of how multicomponent non-enzymatic reactions can occur through inherently reactive bacterial metabolites.

Chemoselective Henry Condensations Catalyzed by Artificial Carboligases

Garrabou, Xavier,Macdonald, Duncan Stuart,Hilvert, Donald

, p. 6001 - 6003 (2017)

The promiscuity of de novo designed enzymes provides a privileged platform for diverse abiological reactions. In this work, we report the first example of a nitroolefin synthase that catalyzes the Henry condensation between aromatic aldehydes and nitromethane. Significant catalytic activity was discovered in the computationally designed and evolved carboligase RA95.5-8, and mutations around the active site were shown to improve the reaction rate, demonstrating the potential to optimize the enzyme by directed evolution. This novel nitroolefin synthase could participate in complex biological cascades, whereby the highly tunable chemoselectivity could afford useful synthetic building blocks.

Highly selective electrocatalytic dehydrogenation at low applied potential catalyzed by an Ir organometallic complex

Bonitatibus, Peter J.,Rainka, Matthew P.,Peters, Andrea J.,Simone, Davide L.,Doherty, Mark D.

, p. 10581 - 10583 (2013)

A homogeneous organometallic Ir complex was shown to catalyze the electro-oxidation of 4-methoxybenzyl alcohol to p-anisaldehyde at a very low applied potential with remarkably high selectivity and Faradaic efficiency. In the chemical catalysis, when stoi

Ostensible enzyme promiscuity: Alkene cleavage by peroxidases

Mutti, Francesco G.,Lara, Miguel,Kroutil, Markus,Kroutil, Wolfgang

, p. 14142 - 14148 (2010)

Enzyme promiscuity is generally accepted as the ability of an enzyme to catalyse alternate chemical reactions besides the 'natural' one. In this paper peroxidases were shown to catalyse the cleavage of a C=C double bond adjacent to an aromatic moiety for selected substrates at the expense of molecular oxygen at an acidic pH. It was clearly shown that the reaction occurs due to the presence of the enzyme; furthermore, the reactivity was clearly linked to the hemin moiety of the peroxidase. Comparison of the transformations catalysed by peroxidase and by hemin chloride revealed that these two reactions proceed equally fast; additional experiments confirmed that the peptide backbone was not obligatory for the reaction and only a single functional group of the enzyme was required, namely in this case the prosthetic group (hemin). Consequently, we propose to define such a promiscuous activity as 'ostensible enzyme promiscuity'. Thus, we call an activity that is catalysed by an enzyme 'ostensible enzyme promiscuity' if the reactivity can be tracked back to a single catalytic site, which on its own can already perform the reaction equally well in the absence of the peptide backbone.

A hydrophilic covalent organic framework for photocatalytic oxidation of benzylamine in water

Liu, Ziqian,Su, Qing,Ju, Pengyao,Li, Xiaodong,Li, Guanghua,Wu, Qiaolin,Yang, Bing

, p. 766 - 769 (2020)

The highly hydrophilic COF material (TFPT-BMTH) was constructed by pore surface functionalizing strategy, and exhibited excellent porosity, high crystallinity, and good thermal and chemical stability. The resulting COF exhibits significant catalytic activity and recyclability together with environmental benignity in photocatalytic oxidation of benzylamine in water under ambient conditions.

Tetra-porphyrin molecular tweezers: Two binding sites linked: Via a polycyclic scaffold and rotating phenyl diimide core

Murphy,Norman,White,Perkins,Johnston

, p. 8707 - 8720 (2016)

The synthesis of a tetra-porphyrin molecular tweezer with two binding sites is described. The bis-porphyrin binding sites are aligned by a polycyclic scaffold and linked via a freely rotating phenyl diimide core. Synthesis was achieved using a divergent approach employing a novel coupling method for linking two polycyclic units to construct the core, with a copper(ii)-mediated phenyl boronic acid coupling found to extend to our polycyclic imide derivative. We expect this chemistry to be a powerful tool in accessing functional polycyclic supramolecular architectures in applications where north/south reactivity and/or directional interactions between modules are important. Porphyrin receptor functionalisation was undertaken last, by a four-fold ACE coupling reaction on the tetra-epoxide derivative of the core.

A convenient deprotection of 1,3-dithiane derivatives with ferric nitrate under heterogeneous conditions

Hirano, Masao,Ukawa, Ken,Yakabe, Shigetaka,Morimoto, Takashi

, p. 1527 - 1533 (1997)

1,3-Dithianes derived from aromatic, aliphatic, and alicyclic ketones or aldehydes can be conveniently converted to the parent carbonyl compounds with a combination of ferric nitrate and silica gel in hexane in excellent to quantitative yields.

Manganese(III) corrole catalyzed selective oxidation of alcohols to carbonyl compounds by tert-butyl hydroperoxide under mild condition

Bose, Suranjana,Pariyar, Anand,Biswas, Achintesh Narayan,Das, Purak,Bandyopadhyay, Pinaki

, p. 446 - 449 (2011)

Mild oxidation of alcohols has been achieved with tert-butylhydroperoxide catalyzed by electron deficient manganese(III) corroles at room temperature. The catalysts used in this study showed high activity in the oxidation of benzylic alcohols to the corre

Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants

Bera, Smritilekha,Gupta, Shilpi,Mondal, Dhananjoy

, (2020)

Organic reactions in the aqueous environment have recently emerged as a promising research area. The generation of nascent-HBr from the slow hydrolysis of the dispersed catalyst, benzyl bromide, with the interior water present in the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcohols, and hydroxylated acyclic compounds in good to excellent yields.

An Electrochemical Evidence for the Participation of Iron(IV) Porphyrin Species in the C-C Bond Cleavage of 1,2-Diaryl-1,2-ethanediol

Okamoto, Tadashi,Sasaki, Ken,Takano, Mikio,Oka, Shinzaburo

, p. 415 - 416 (1988)

Cyclic voltammogram of as mixture of tetraphenylporphrinatoiron(III) and 1,2-bis(4-methoxyphenyl)ethane-1,2-diol in dichloromethane showed a catalytic wave at the potential corresponding to the oxidation of Fe(III) to Fe(IV).The rate of reaction of Fe(IV) with the diol following the electrochemical process was determined.

Outstanding response of carbon nitride photocatalysts for selective synthesis of aldehydes under UV-LED irradiation

Lopes, Joana C.,Sampaio, Maria J.,Fernandes, Raquel A.,Lima, Maria J.,Faria, Joaquim L.,Silva, Cláudia G.

, p. 32 - 38 (2020)

The photocatalytic conversion of alcohols into the corresponding aldehydes constitutes an important reaction in organic synthesis. Optical semiconductors based on carbon nitride were prepared by thermal condensation of dicyandiamide followed by a thermal

The Oxidation of Akoxytributylstannanes with Copper(II) Bromide

Yamaguchi, Jun-ichi,Takeda, Takeshi

, p. 423 - 426 (1992)

The oxidation of alkoxytributylstannanes with copper(II) bromide in the presence of lithium bromide and t-butoxytributylstannane gave the corresponding carbonyl compounds in good yields under mild reaction conditions.

Transition metal-free and substrate-selective oxidation of alcohols using water as an only solvent in the presence of β-cyclodextrin

Ji, Hong-Bing,Shi, Dong-Po,Shao, Ming,Li, Zhong,Wang, Le-Fu

, p. 2517 - 2520 (2005)

A facile, substrate-selective and transition metal-free oxidation of benzylic and allylic alcohols catalyzed by β-cyclodextrin with NaOCl oxidant using water as an only solvent was developed.

Aerobic dehydrogenative imination in complete aqueous media catalyzed by poly(aniline sulfonic acid)/gold nanoparticles

Amaya, Toru,Ito, Tsubasa,Hirao, Toshikazu

, p. 2409 - 2411 (2013)

Dehydrogenative imination in aqueous media was achieved using poly(2-methoxyaniline-5-sulfonic acid) (PMAS)/gold nanoparticles, where PMAS worked as a redox mediator.

Chemoselective aerobic oxidation of primary alcohols catalyzed by a ruthenium complex

Miyata, Atsushi,Murakami, Masakazu,Irie, Ryo,Katsuki, Tsutomu

, p. 7067 - 7070 (2001)

In the presence of secondary alcohols, primary alcohols are selectively oxidized to aldehydes under aerobic conditions by using a (nitrosyl)Ru(salen) complex as catalyst.

One-pot conversion of activated alcohols into 1,1-dibromoalkenes and terminal alkynes using tandem oxidation processes with manganese dioxide

Quesada, Ernesto,Raw, Steven A.,Reid, Mark,Roman, Estelle,Taylor, Richard J.K.

, p. 6673 - 6680 (2006)

Approaches to the preparation of C1-homologated dibromoalkenes and terminal alkynes from activated alcohols using one-pot tandem oxidation processes (TOPs) with manganese dioxide are outlined. The conversion of alcohols into dibromoalkenes is described using dibromomethyltriphenylphosphonium bromide and the formation of terminal alkynes was achieved via a sequential one-pot, two-step process utilising the Bestmann-Ohira reagent.

Thermotropic phase transitions in 5,15-bis(4-alkoxyphenyl)octaalkylporphyrins

Sudhoelter, Ernst J. R.,Van Dijk, Marinus,Teunis, Cees J.,Sanders, Georgine M.,Harkema, Sybolt,Van De Velde, Gerrit M. H.,Schouten, Pieter G.,Warman, John M.

, p. 357 - 363 (1996)

Nineteen novel alkyl substituted porphyrins have been synthesized and their thermal phase behaviour has been investigated in detail. Twelve compounds showed a reversible phase transition below the isotropization temperature. From time resolved microwave conductivity (TRMC) measurements and powder X-ray diffractometry it was concluded that the molecular packing does not change significantly at the lower phase transition temperature and that the porphyrin cores occupy isolated positions. Single X-ray diffraction measurements showed that the porphyrins are arranged in a layered structure and that the space between the layers is occupied by the alkyl substituents of the pyrrole units. The phase transitions at the lower temperature were therefore identified as changes in the crystal ordering of the porphyrins.

Total Synthesis of Biselyngbyaside

Sato, Eisuke,Sato, Miho,Tanabe, Yurika,Nakajima, Naoya,Ohkubo, Akifumi,Suenaga, Kiyotake

, p. 6770 - 6777 (2017)

The first total synthesis of biselyngbyaside, an 18-membered macrolide glycoside, was achieved. The glycoside bond was introduced using the Schmidt method before construction of the 18-membered ring due to the instability of the conjugated diene and the β

Optimization of a biocatalytic single-step alkene cleavage of aryl alkenes

Mang, Harald,Gross, Johannes,Lara, Miguel,Goessler, Christian,Schoemaker, Hans E.,Guebitz, Georg M.,Kroutil, Wolfgang

, p. 3350 - 3354 (2007)

The oxidative cleavage of a C{double bond, long}C double bond adjacent to an aryl moiety was achieved in the presence of a protein preparation of Trametes hirsuta G FCC 047 to yield the corresponding aldehydes. Molecular oxygen was the only oxidant required. All positive substrates had a C{double bond, long}C bond conjugated to an aromatic system, all other compounds tested not fulfilling this requirement were non-substrates. The optimum reaction conditions are 20 °C, pH 6-6.5, 15% v/v ethanol as co-solvent at an apparent oxygen pressure of 2 bar.

Metal Ion-Driven Constitutional Adaptation in Dynamic Covalent C=C/C=N Organo-Metathesis

Gu, Ruirui,Lehn, Jean-Marie

, p. 44 - 48 (2021)

Knoevenagel barbiturate derivatives and imines are able to undergo efficient component recombination through dynamic covalent C=C/C=N organo-metathesis in absence of a catalyst. A [2×2] dynamic covalent library (DCL) containing two Knoevenagel derivatives Kn1 and Kn2 and two imines A1 and A2 has been established and its adaptive features in response to the addition of metal cations have been investigated. Addition of Cu(I) triflate as an effector, induces fast and remarkable constitutional selection of the DCL towards amplification of the Cu(I)-A2 complex and its agonist Kn1. This adaptation process could be reversed by addition of neocuproine as a competitive Cu(I) ligand. Furthermore, separate addition of five other metal cations as input agents, i. e. Ag(I), Fe(II), Zn(II), Cu(II) and Li(I), led to the generation of cation-specific distribution patterns as outputs, showing the ability of the present DCL to recognize different effectors.

Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water

Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David

, (2021/11/30)

Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.

Visible-Light-Induced Selective C-C Bond Cleavage Reactions of Dimeric β-O-4 and β-1 Lignin Model Substrates Utilizing Amine-Functionalized Fullerene

Cho, Dae Won,Jang, Hannara,Kim, Min-Ji,Kim, Young-Il,Lim, Dong Hyun,Lim, Suk Hyun,Wee, Kyung-Ryang

, p. 2289 - 2300 (2022/02/07)

Finding a selective and efficient fragmentation process under ambient conditions is pivotal for the generation of fuels and chemical feedstocks from lignoceullosic biomass. In the present study, visible-light and amine-functionalized fullerene-based photocatalyst-promoted photodegradation reactions of dimeric β-O-4 and β-1 lignin model compounds, containing varying numbers of methoxy substituents on the arene ring, were explored to find and develop mild, eco-friendly photochemical techniques for efficient delignification. The results showed that, in contrast to well-known organic photoredox catalysts, amine-functionalized fullerene photocatalyst promoted photochemical reactions of lignin model compounds could lead to more efficient lignin fragmentation reactions through a pathway involving a selective Cα-Cβ bond cleavage process, and in addition, Cα-hydroxyl moiety in lignin model compounds played a significant role in the success of the Cα-Cβ bond cleavage reaction of lignin model substrates.

Lessons from an Array: Using an Electrode Surface to Control the Selectivity of a Solution-Phase Chemical Reaction

Feng, Enqi,Jing, Qiwei,Moeller, Kevin D.

supporting information, (2022/01/26)

Electrochemistry offers a variety of novel means by which selectivity can be introduced into synthetic organic transformations. In the work reported, it is shown how methods used to confine chemical reactions to specific sites on a microelectrode array can also be used to confine a preparative reaction to the surface of an electrode inserted into a bulk reaction solution. In so doing, the surface of a modified electrode can be used to introduce new selectivity into a preparative reaction that is not observed in the absence of either the modified electrode surface or the effort to confine the reaction to that surface. The observed selectivity can be optimized in the same way that confinement is optimized on an array and is dependent on the nature of the functionalized surface.

Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents

Antony, Jesna,Mathai, Sindhu,Natarajan, Rakesh,P. Musthafa, Sumi,Rappai, John P.,S. Devaky, Karakkattu

supporting information, (2022/02/25)

We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.

Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride

Azeez, Sadaf,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri

supporting information, p. 2048 - 2053 (2022/03/31)

A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.

Process route upstream and downstream products

Process route

1-methoxy-4-(3-phenyl-1-propen-1-yl)benzene
35856-81-6,20442-74-4

1-methoxy-4-(3-phenyl-1-propen-1-yl)benzene

phenylacetaldehyde
122-78-1

phenylacetaldehyde

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
bei der Ozonolyse;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
durch elektrolytische Oxydation in neutraler, saurer oder alkalischer waessriger Suspension;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
With hydrogenchloride; sodium chlorite; water; at 20 ℃; for 0.0833333h;
83%
7%
With sodium hypochlorite; In acetonitrile; for 0.5h; Ambient temperature;
37%
52%
With [hydroxy(tosyloxy)iodo]benzene; water; In dimethyl sulfoxide; at 20 ℃; for 24h;
47%
25%
With tetrabutylammomium bromide; dihydrogen peroxide; phosphotungstic acid; In dichloromethane; water; at 20 ℃; for 24h; Further Variations:; Catalysts; Reagents; Solvents; reaction time; Product distribution;
10%
10%
p-methylanizole
104-93-8

p-methylanizole

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

methoxybenzene
100-66-3

methoxybenzene

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
With thallium(I) oxide; oxygen; vanadia; at 430 ℃; other p-substituted toluenes;
p-methylanizole
104-93-8

p-methylanizole

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxy-phenol
150-76-5

4-methoxy-phenol

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

Conditions
Conditions Yield
With water; iron; trifluoroacetic acid; In pyridine; for 1h; Rate constant;
With water; iron; trifluoroacetic acid; In acetone; for 1h; Rate constant;
With water; copper; trifluoroacetic acid; In pyridine; for 1h; Rate constant;
With water; copper; trifluoroacetic acid; In acetone; for 1h; Rate constant;
p-methylanizole
104-93-8

p-methylanizole

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate; In acetonitrile; at 25 ℃; for 6h; under 760 Torr;
9%
80%
With oxygen; 9,10-Dicyanoanthracene; Paraquat; iron(II) chloride; In methanol; acetonitrile; for 3.3h; Ambient temperature; Irradiation;
15%
78%
With pyridine; dipotassium peroxodisulfate; copper(I) sulfate; In water; acetonitrile; at 65 - 70 ℃; for 3h;
18%
70%
With N-hydroxyphthalimide; oxygen; In acetic acid; at 90 ℃; for 2h;
35.1%
47.3%
With oxygen; titanium(IV) oxide; silver sulfate; In acetonitrile; for 2h; Ambient temperature; Irradiation;
7%
43%
With chromium(VI) oxide; periodic acid; In acetonitrile; at 20 ℃; for 1h;
34%
7%
With gallium(III) oxide; oxygen; vanadia; titanium(IV) oxide; at 399.9 ℃; Yield given. Yields of byproduct given;
With oxygen; vanadia; titanium(IV) oxide; zirconium(IV) oxide; at 399.9 ℃; Product distribution; other reagents;
With Coprinus sp. peroxidase; tartaric acid buffer; dihydrogen peroxide; In water; acetone; at 20 ℃; pH=5;
With oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; acetone oxime; at 80 ℃; for 9h; Ionic liquid;
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate; at 80 ℃; under 760.051 Torr; Ionic liquid;
With N-hydroxyphthalimide; oxygen; In acetonitrile; at 80 ℃; for 18h; under 760.051 Torr; Schlenk technique;
With tert.-butylhydroperoxide; In water; at 80 ℃; for 12h; Sealed tube;
With oxygen; N-hydroxy-1,6-methano[10]annulene-3,4-dicarboximide; cobalt(II) acetate; In acetic acid; at 100 ℃; for 20h; under 750.075 Torr;
80 %Chromat.
6 %Chromat.
With cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen; acetylacetone; In acetonitrile; at 165 ℃; for 4h; under 7500.75 Torr; Autoclave;
p-methylanizole
104-93-8

p-methylanizole

p-methoxybenzyl acetate
104-21-2

p-methoxybenzyl acetate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
With oxygen; cobalt(II) acetate; In acetic acid; at 110 ℃; for 3h; under 2280 Torr;
p-methylanizole
104-93-8

p-methylanizole

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

Conditions
Conditions Yield
With oxygen; cobalt(II) acetate; chromium(lll) acetate; In acetic acid; at 110 ℃; for 3h; under 2280 Torr;
1.6 % Chromat.
3.6 % Chromat.
p-methylanizole; With manganese(IV) oxide; C32H16N8O4Ru; C46H39CrN12O2; at 168 ℃; under 10501.1 Torr;
With water; at 125 ℃; under 7500.75 Torr;
With cobalt(II) acetate monohydrate; 2,2'-azobis(isobutyronitrile); oxygen; In neat (no solvent); at 80 ℃; for 15h; under 760.051 Torr; Temperature; Concentration; Solvent;
2-(4-methoxyphenyl)-1,3-oxathiolane
22391-03-3

2-(4-methoxyphenyl)-1,3-oxathiolane

2-carboxybenzene diazonium chloride
4661-46-5

2-carboxybenzene diazonium chloride

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

phenylthioethylene
1822-73-7

phenylthioethylene

Conditions
Conditions Yield
With methyloxirane; In 1,2-dichloro-ethane; for 0.75h; Heating;
50%
76%
With methyloxirane; In 1,2-dichloro-ethane; for 0.75h; Mechanism; Heating;
50%
76%
dichloromethane
75-09-2

dichloromethane

4,4'-dimethoxystilbene
4705-34-4

4,4'-dimethoxystilbene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxy-phenol
150-76-5

4-methoxy-phenol

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
With oxygen; ozone; Yield given. Multistep reaction; 2.) methanol;
10 % Chromat.
0.12 g
With oxygen; ozone; Yield given. Multistep reaction; 2.) methanol;
90 % Chromat.
0.12 g
With oxygen; ozone; Yield given. Multistep reaction; 2.) methanol;
90 % Chromat.
10 % Chromat.

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