38574-09-3Relevant articles and documents
Synthesis of Functionalized Aliphatic Acid Esters via the Generation of Alkyl Radicals from Silylperoxyacetals
Matsumoto, Akira,Shiozaki, Yoko,Sakurai, Shunya,Maruoka, Keiji
supporting information, p. 2431 - 2434 (2021/08/07)
We describe a catalytic method for the synthesis of a variety of functionalized aliphatic acid esters using silylperoxyacetals, which are versatile alkyl radical precursors with a terminal ester moiety. In the presence of an appropriate transition-metal catalyst, the in situ generation of alkyl radicals and the subsequent bond-forming process proceeds smoothly to afford synthetically valuable aliphatic acid derivatives. The present method can be applied to the efficient synthesis of a pharmaceutically important 1,1-diarylalkane motif. In addition, a novel strategy for the synthesis of structurally diverse hydroxy acid derivatives via a C?O bond formation process that utilizes TEMPO has been developed.
A mild route to solid-supported rhodium nanoparticle catalysts and their application to the selective hydrogenation reaction of substituted arenes
Moreno-Marrodan, Carmen,Liguori, Francesca,Mercadé, Elisabet,Godard, Cyril,Claver, Carmen,Barbaro, Pierluigi
, p. 3762 - 3772 (2015/07/01)
A clean route is described for the preparation of 1.3% (w/w) supported rhodium nanoparticle (3.0 ± 0.7 nm) catalysts onto commercial ion-exchange resins. Their application to the liquid-phase hydrogenation reaction of C=C bonds shows the most active species are obtained under catalytic conditions at room temperature and 1 bar H2. The heterogeneous catalyst shows excellent activity, selectivity and reusability in the hydrogenation reaction of alkenes and substituted arenes under very undemanding conditions. The results are discussed in terms of support effect on the catalytic efficiency.
Iron(III) tosylate in the preparation of dimethyl and diethyl acetals from ketones and β-keto enol ethers from cyclic β-diketones
Mansilla, Horacio,Afonso, Maria M.
, p. 2607 - 2618 (2008/12/22)
An efficient method for conversion of ketones to their corresponding dimethyl and diethyl acetals and of cyclic β-diketones into β-keto enol ethers using Fe(OTs)3 as a catalyst is described. Copyright Taylor & Francis Group, LLC.
High stereoselectivity in chelation-controlled intermolecular Heck reactions with aryl chlorides, vinyl chlorides and vinyl triflates
Datta, Gopal K.,Larhed, Mats
, p. XX674-676 (2008/09/17)
Highly stereoselective chelation-controlled Pd(0)-catalyzed β-arylations and β-vinylations of a five-membered chiral, pyrrolidine-based vinyl ether were achieved using aryl- and vinyl chlorides as substrates, yielding quaternary 2-aryl/vinyl-2-methyl cyclopentanones in 89-96% ee under neutral reaction conditions. This journal is The Royal Society of Chemistry.
Simple method for the preparation of dimethyl acetals from ketones with montmorillonite K 10 and p-toluenesulfonic acid
Mansilla, Horacio,Regas, David
, p. 2195 - 2201 (2007/10/03)
A simple method for conversion of ketones to their corresponding dimethyl acetals using montmorillonite K 10 and p-toluenesulfonic acid as acidic cocatalysts under very mild reaction conditions is described. Copyright Taylor & Francis Group, LLC.
High-pressure-promoted uncatalyzed ketalization of ketones and oxy-Michael/ketalization of conjugated enones
Kumamoto, Koji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
, p. 2254 - 2256 (2007/10/03)
A new practical method for ketalization or oxy-Michael/ketalization was developed using the high-pressure-promoted condensation of ketones or α,β-unsaturated ketones with alcohols in the presence of trialkyl orthoformates as water scavengers. Georg Thieme Verlag Stuttgart.
Synthesis of tetrahydro-2(1H)quinazolinones, cyclopenta[d]-2(1H) pyrimidinones, and their thioxo analogs from 2-trifluoroacetyl-1- methoxycycloalkenes
Bonacorso, Helio G.,Costa, Michelle B.,Lopes, Itamar S.,Oliveira, Marli R.,Drekener, Roberta L.,Martins, Marcos A. P.,Zanatta, Nilo,Flores, Alex F. C.
, p. 3055 - 3064 (2007/10/03)
A series of six (8)-alkyl-4-trifluoromethyl-5,6,7,8-tetrahydro-2(1 H)quinazolinones, 4-trifluoromethyl-cyclopenta[d]-2(1 H)pyrimidinones, and their thioxo analogs from the reaction of five β-alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan-2-ol as solvent and boron trifluoride diethyl etherate as catalyst in 18-65% yield. Copyright Taylor & Francis, Inc.
Synthesis, 17O NMR spectroscopy and structure of 2-trifluoroacetyl-1-methoxycycloalkenes
Bonacorso, Helio G.,Costa, Michelle B.,Moura, Sidnei,Pizzuti, Lucas,Martins, Marcos A.P.,Zanatta, Nilo,Flores, Alex F.C.
, p. 1396 - 1402 (2007/10/03)
Among the synthesis of a series of five well-known 2-trifluoroacetyl-1- methoxycycloalkenes derived from cyclopentanone and substituted cyclohexanones, this paper describes the synthesis of three new 2-trifluoroacetyl-1- methoxycycloalkenes derived from cycloheptanone, cyclooctanone and cyclododecanone in 60-68% yield. Subsequently, the 17O NMR chemical shift analysis of the carbonyl and the methoxy groups for these cyclic molecules clearly showed the electron push-pull phenomenon and revealed large and irregular variations of 17O NMR chemical shifts with the ring size. Finally, a more stable conformation of these trifluoroacetyl-containing cycloalkenes was determined by energy minimization calculations using Austin Model 1 (AM1) semi-empirical method and correlations between 17O NMR data and torsion angles or oxygen net charge calculated by AM1 semi-empirical method were performed.
Photochemical acetalization of carbonyl compounds in protic media using an in situ generated photocatalyst
De Lijser, H.J. Peter,Rangel, Natalie Ann
, p. 8315 - 8322 (2007/10/03)
Carbonyl compounds are conveniently converted into their corresponding dimethyl acetals in good yields and short reaction times by means of a photochemical reaction in methanol with a catalytic amount of chloranil (2,3,5,6-tetrachloro-1,4-benzoquinone, CA) as the sensitizer. Using aldehydes gives better results than using ketones, which also tend to form enol ethers as side products. These results are similar to those of simple acid-catalyzed acetalization reactions, suggesting the involvement of a photochemically generated acid. On the basis of steady state and laser flash photolysis data the reaction is proposed to involve the in situ generation of a photocatalyst (2,3,5,6-tetrachloro-1,4-hydroquinone, TCHQ) via reaction of CA with the solvent. The acetalization process is initiated by ionization of TCHQ, followed by loss of a proton to the solvent or the carbonyl, which starts a catalytic reaction. The photocatalyst is regenerated via a disproportionation reaction.
Synthesis of peroxide compounds by the BF3-catalyzed reaction of acetals and enol ethers with H2O2
Terent'ev,Kutkin,Platonov,Vorontsov,Antipin,Ogibin,Nikishin
, p. 681 - 687 (2007/10/03)
Aliphatic and alicyclic gem-bis-hydroperoxides and their derivatives, bis(1-hydroperoxycycloalkyl) and bis(1-hydroperoxyalkyl) peroxides, dispiro- and tetraalkyl-1,2,4,5-tetroxanes were synthesized by the reaction of aliphatic and alicyclic acetals and enol ethers with H2O2 in the presence of BF3 in anhydrous Et2O.
