133320-07-7Relevant articles and documents
Richardson et al.
, p. 6652,6657 (1974)
Synthesis of Pd catalysts based on a nonbornene - CO copolymer and their properties in the carbomethoxylation of propylene
Korneeva,Kerov,Ibragimova,Kurkin,Makovetsky,Slivinsky
, p. 360 - 362 (1998)
It was found that carboxylation of norbornene (nbn) in the presence of the PdCl2 -PPh3 - HCl catalytic system is accompanied by alternating copolymerization of nbn with carbon monoxide to form norbornanecarboxylic acid (yield -20%) and a nbn-CO copolymer (yield -80%, Mw = 1600, Mw/Mn = 1.6). The PdII salt of poly(norbornaneketone)carboxylic acid is a highly active catalyst for the carbomethoxylation of propylene.
Selective carbonylation of Propane in Superacid Media via Hydride Abstraction by the Chlorocarbocations: CCl3+ and CHCl2+
Culmann, Jean-Christophe,Simon, Michael,Sommer, Jean
, p. 1098 - 1100 (1990)
Carbonylation of propane in HF-SbF5 (5:1 molar ratio) superacid in the presence of carbon tetrachloride (or chloroform) at -30 deg C yields exclusively the isobutyryl ion (isopropyloxocarbenium ion), analysis of the gaseous fluorocarbons generated as side products showing both hydride abstraction by CCl3+ (or CHCl2+) and Cl/F exchange on the tri- and di-chloromethane formed; in the absence of CCl4 (or(CHCl3) no reaction takes place under the same experimental conditions.
Thermochemical Studies of Carbonyl Compounds. 3. Enthalpies of Hydrolysis of Ortho Esters
Wiberg, Kenneth B.,Martin, Eric J.,Squires, Robert R.
, p. 4717 - 4720 (1985)
The enthalpies of hydrolysis of a series of ortho esters have been measured in aqueous dioxane.The largest effect on ΔHr was found with α-branching, in contrast to the previously reported hydrolysis of ketals which gave the larger effect with β-branching.Possible reasons for this difference in behavior are discussed.
Transition Metal Ketene Complexes as Active Intermediate for Catalytic Carbonylation of Geminal Dibromoalkanes
Miyashita, Akira,Kihara, Takehiro,Nomura, Kotohiro,Nohira, Hiroyuki
, p. 1607 - 1610 (1986)
MX2(PPh3)2 (M=Ni, Pd, Pt; X=Cl, Br) and Co2(CO)8 catalyze alkoxy- and aminocarbonylation of geminal dibromoalkanes, R1R2CBr2 (R1, R2=H and CH3).In the course of the catalysis, initial formation of the transition metal ketene complexes, M(CH2=C=O)L2, was followed by the reaction with alcohols to yield carbalkoxymethyl metal intermediate leading to esters.
Ozonolytic decyclization of (R)-4-menthen-3-one
Kharisov,Gazetdinov,Botsman,Muslukhov,Ishmuratov,Tolstikov
, p. 1005 - 1008 (2002)
Ozonolytic decyclization of (R)-4-menthen-3-one is accompanied by fragmentation of the isobutyl group, leading to ω-functionalized 3-methylpentanoic acid derivatives.
C(9)-C Bonds of 10-Methyl-9-alkyl-9,10-dihydroacridines Acting Like Metal-Carbon Bonds in the Reactions with Electrophiles
Fukuzumi, Shunichi,Tokuda, Yoshihiro,Fujita, Morifumi,Otera, Junzo,Chanon, Michel,et al.
, p. 1701 - 1704 (1992)
The C(9)-C bonds of 10-methyl-9-alkyl-9,10-dihydroacridines (AcrHR: R = CMe2COOMe, CMe(H)COOEt, But, CHPh2) are readily cleaved by electrophiles (perchloric acid, oxygen, and iodine) in acetonitrile at 298 K, acting like metal-carbon bonds to yield the corresponding alkane, alkyl hydroperoxide, and alkyl iodide, respectively.
A Simple Method for the Esterification of Carboxylic Acids Using Chlorosilanes
Nakao, Ren,Oka, Kunio,Fukumoto, Tsugio
, p. 1267 - 1268 (1981)
Various carboxylic esters, including some with bulky substituents, are prepared in good yields from carboxylic acids and alcohols under mild conditions by the use of trimethylchlorosilane, dimethyldichlorosilane, methyltrichlorosilane, or tetrachlorosilane.
Synthesis of β2,2-Amino Esters via Rh-Catalysed Regioselective Hydroaminomethylation
Cunillera, Anton,Ruiz, Aurora,Godard, Cyril
, p. 4201 - 4207 (2019)
The synthesis of β2,2-amino esters was successfully achieved via Rh-catalysed regioselective hydroaminomethylation of methyl methacrylate with secondary amines using the neutral precursor [Rh(acac)(CO)2]. In this process, the presence of molecular sieves revealed crucial in order to access the final amino ester. For the synthesis of products containing aniline derivatives, the use of the cationic precursor [Rh(COD)2]BF4 and MeCgPPh phosphine as ligand was necessary in a mixture of toluene/DCE as solvent. Effects of the steric and electronic properties of the amines were observed during this study. Interestingly, poisoning effect of CO in the hydrogenation of the imine intermediate was observed when benzyl amine was used. (Figure presented.).
Boosting homogeneous chemoselective hydrogenation of olefins mediated by a bis(silylenyl)terphenyl-nickel(0) pre-catalyst
Lücke, Marcel-Philip,Yao, Shenglai,Driess, Matthias
, p. 2909 - 2915 (2021/03/14)
The isolable chelating bis(N-heterocyclic silylenyl)-substituted terphenyl ligand [SiII(Terp)SiII] as well as its bis(phosphine) analogue [PIII(Terp)PIII] have been synthesised and fully characterised. Their reaction with Ni(cod)2(cod = cycloocta-1,5-diene) affords the corresponding 16 VE nickel(0) complexes with an intramolecularη2-arene coordination of Ni, [E(Terp)E]Ni(η2-arene) (E = PIII, SiII; arene = phenylene spacer). Due to a strong cooperativity of the Si and Ni sites in H2activation and H atom transfer, [SiII(Terp)SiII]Ni(η2-arene) mediates very effectively and chemoselectively the homogeneously catalysed hydrogenation of olefins bearing functional groups at 1 bar H2pressure and room temperature; in contrast, the bis(phosphine) analogous complex shows only poor activity. Catalytic and stoichiometric experiments revealed the important role of the η2-coordination of the Ni(0) site by the intramolecular phenylene with respect to the hydrogenation activity of [SiII(Terp)SiII]Ni(η2-arene). The mechanism has been established by kinetic measurements, including kinetic isotope effect (KIE) and Hammet-plot correlation. With this system, the currently highest performance of a homogeneous nickel-based hydrogenation catalyst of olefins (TON = 9800, TOF = 6800 h?1) could be realised.
Iron-catalysed 1,2-aryl migration of tertiary azides
Wei, Kaijie,Yang, Tonghao,Chen, Qing,Liang, Siyu,Yu, Wei
supporting information, p. 11685 - 11688 (2020/10/19)
1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.
PH-Responsive Pickering emulsion stabilized by polymer-coated silica nanoaggregates and applied to recyclable interfacial catalysis
Dong, Jinfeng,Luo, Ruidong,Luo, Yunbai
, p. 42423 - 42431 (2020/12/09)
We first synthesized a diblock copolymer poly[tert-butyl methacrylate]-b-poly[3-(trimethoxysilyl)propyl methacrylate] (PtBMA-b-PTMSPMA) through reversible addition-fragmentation chain transfer (RAFT) living radical polymerization and grafted it onto fumed silica by converting the PTMSPMA segment to silanol and the PtBMA segment to polymethylacrylic acid (PMAA) in the presence of trifluoroacetic acid in order to obtain PMAA brush-coated silica nanoaggregates P-Si. TEM, DLS, FTIR, and TGA results confirmed the successful modification of the starting materials. The nanoaggregates flocculated and stabilized a toluene-in-water Pickering emulsion at low pH, while the nanoaggregates were well dispersed in water and broke the emulsion under both neutral and basic conditions. Alternatively, the addition of acid/base induced emulsification/demulsification cycles that were sustained for several cycles. Moreover, when the P-Si was mixed with Rh-loaded silica, Rh-Si, the mixture had the same pH-responsive Pickering emulsion behavior as the single P-Si. This Pickering emulsion system can be used in the biphasic interfacial catalytic hydrogenation of olefins and had excellent yields under a hydrogen atmosphere. The yield of Pickering emulsion catalysis rapidly reached more than 99% in 3 h, while that of the demulsified mixture failed to reach 20% in 4 h, which verified the promotion of catalysis by the Pickering emulsion. Base-induced demulsification can be used to separate the products and recycle the catalyst. This pH-responsive Pickering emulsion catalytic system was capable of several cycles of reuse, and there was no significant decrease in catalytic efficiency even after eight cycles. This journal is
