cyclic anhydride reaction with amine


95 %, but ca. 9 % with KPS. Ketene yields near 80% are apparently attainable with the tri-1-butylamine complexes of Et 3 Al, Bu i 3 Al and Bu 3 Al. Kas’yan, A.O., Krishchik, O.V., Umrykhina, L.K., and Kas’yan, L.I., Zh. Dnepropetrovsk National University, Dnepropetrovsk, 49625, Ukraine, L. I. Kas’yan, V. A. Pal’chikov & I. N. Tarabara, Ukraine State University of Chemical Engineering, Dnepropetrovsk, Ukraine, Institute of Organic Chemistry at Rhein-Westfalen Technical University, Aachen, Germany, Research and Development Enterprise Single Crystals Institute, Ukrainian Academy of Sciences, Kharkov, Ukraine, You can also search for this author in Kas’yan, L.I., Pal’chikov, V.A., Tarabara, I.N. 3, p. 87. Cyclic acid anhydride reactions with triorganoaluminum compounds account for most of the literature in this area. Shohei Inoue, Takuzo Aida, in Comprehensive Polymer Science and Supplements, 1989, The alternating copolymerization between epoxide (1) and cyclic acid anhydride (2) proceeds in the presence of a catalyst, such as inorganic and organic salts, organometallic compounds and Lewis bases, producing polyester (3) under rather rigorous conditions (equation 1).4 A recent development of particular interest is the discovery of the catalyst system composed of aluminum porphyrin [4; (TPP)AIX, where (TPP) = 5, 10, 15, 20-tetraphenylporphinato)] and a quaternary organic salt, which gives the alternating copolymer (3) of controlled molecular weight with narrow molecular weight distribution under mild conditions.5,6. Reasons for the influence of polymer‐bound chemical functionality on the reaction rates for these amines are discussed. Chem., 1990, vol. These reducing groups, linked to the surface of silica, were introduced by reactions of surface silanol groups with 3-glycidoxypropyltrimethoxysilane (GPS), 3-aminopropyltriethoxysilane (APS), 3-mercaptopropyltrimethoxysilane (MPS), respectively. © 1995 John Wiley & Sons, Inc. AB - The validity of extrapolating the reactivity of low molar mass compounds in solution to the polymer‐analogous chemistry between polymer‐bound functionality is investigated for the reaction of primary amines with cyclic anhydrides in the moderately polar solvents, anisole and tetraethyleneglycol dimethylether. Other polysubstituted 5-vinyl-2H-pyran-2-ones arise in moderate-to-good yields from palladium(II)-mediated reaction of enynoates with electron-deficient alkenes via a selective 6-endo cyclization and alkenylation processes (15OL1636). Scheme 5 shows the case of polymerization of methylmethacrylate on the surface of a positively charged α-A12O3 particle with persulfate. A unique approach has been evolved by Miller. Diphenylketene has been added to trimethylaluminum in benzene solvent to yield a dimeric addition product (equation 102).246 Hydrolysis of this adduct gave 1,1-diphenylacetone. © 1995 John Wiley & Sons, Inc. In neat acetic anhydride at reflux, addition of trialkylaluminum generates ketene in good yield, especially if the trialkylaluminum is strongly complexed. Part 1. The reaction with ammonia. Zh. Polysubstituted 2H-pyran-2-ones are available by oxidative annulation of alkynes and cinnamic acid derivatives catalyzed by an inexpensive ruthenium(II) complex (15OL5264). T. Furuta, T. Kawabata, in Comprehensive Chirality, 2012. Chiral secondary alcohols were acylated with diketene in moderate selectivities (krel up to 6.5) (Scheme 7).17a Before this work, they started a series of work utilizing chiral DMAP analogue in 1995 and reported enantioselective addition of methanol to ketenes and rearrangement of O-acylated enolates of azlactones (oxazol-5(4H)-ones).17b In 1997, Fu reported a kinetic resolution using this series of catalysts on the acylation of alcohols with acetic anhydride and achieved moderate to high selectivity (krel up to 52) (Scheme 8).17c Later, this catalytic method has been applied to the resolution of wide range of allylic alcohols. A pioneering work using chiral phosphines as catalyst for enantioselective acylation was reported by Vedje et al.15 A secondary alcohol was acylated by m-chorolobenzoic anhydride with a moderately high selectivity (krel=15) in the presence of 16 mol% chiral phospholane (Scheme 6). Epoxy can exhibit a wide spectrum of properties by having different combinations of epoxy resins and curing agents. Acetate esters were formed with all the alkoxides except diethylaluminum 2-methyl-2-butanolate. © 2020 Springer Nature Switzerland AG. Saigo, K., Okuda, Y., Wakabayashi, S., Hoshiko, T., and Nohira, H., Chem. Part of Springer Nature. An octapeptide depicted in Figure 3 was discovered from over 100 000 peptide catalysts, which showed high selectivities for acylation of several secondary alcohols.21c. A Novel Reactive Processing Technique: Using Telechelic Polymers To Reactively Compatibilize Polymer Blends. and you may need to create a new Wiley Online Library account. Learn about our remote access options, Monsanto Chemical Company, 730 Worcester St., Springfield, Massachusetts 01151, University of Minnesota, Department of Chemical Engineering and Materials Science, Minneapolis, Minnesota 55455. Kinetic resolution of secondary alcohols using diketene and DMAP analog. Effects on physical and mechanical properties. Search for more papers by this author. Methods of Synthesis), Dnepropetrovsk: Izd. Seebach's protocol for catalytic enantioselective desymmetrization of meso anhydride 8. This is a preview of subscription content, log in to check access. Products of reaction between bicyclo[2.2.1]hept-5-ene-endo-endo-2,3-dicarboxylic anhydride (endic anhydride) and cyclic amines were obtained. 22, N92P. @article{701c6494431e411e91b6ba8b6c2df321. 34, p. 1802. synthesized abietyl glycidyl ether and methyl maleopimarate using one of the rosin acids [143]. Tax calculation will be finalised during checkout. How satisfied are you with the answer? Google Scholar. Important cyclic anhydride curing agents include 1,2-benzenedicarboxylic anhydride (also called phthalic anhydride, PA), 1,2-cyclohexanedicarboxylic anhydride (CHDA), and 1,2,4-benzenetricarboxylic anhydride (BTCA or trimellitic anhydride). By continuing you agree to the use of cookies. Padwa AR, Sasaki Y, Wolske KA, Macosko C. Padwa, Allen R. ; Sasaki, Yoro ; Wolske, Kurt A. ; Macosko, Chris. The product is normally the oxo acid in near 50% yields. Alternatively one mole of aluminum chloride and one mole of alkylaluminum chloride may be used. Radical graft polymerization of acrylamide from ultrafine silica surface was performed in a redox system consisting of ceric ions and reducing agents, such as alcoholic hydroxyl, amino, and mercapto groups, conjugated with the hydroxyl groups on the silica surface.201 As a result, hydrophilic polyacrylamide-grafted silica was synthesized. Resilience improvement of an isotactic polypropylene-g-maleic anhydride by crosslinking using polyether triamine agents. SCHEME 71. Calcium bis(tetra-1-propylaluminate) with acetic anhydride gave very little simple 2-pentanone (the primary addition product).242 The strontium compound gave modest (36%) yields of ketone. found the catalytic activity of NHC in acyl transfer reactions.20a,b Suzuki et al. Products of reaction between bicyclo[2.2.1]hept-5-ene-endo-endo-2,3-dicarboxylic anhydride (endic anhydride) and cyclic amines were obtained. Journal of Polymer Science Part B: Polymer Physics. Scheme 8. 14, p. 306. Scheme 12. Khim., 1967, vol. Chiral DMAP derivatives also reported by Fuji, in 1997.18a They carried out kinetic resolution of monoesters of meso-diols and N-acyl aminoalcohols. Thus, we should all agree that the first step is the nucleophilic attack on the $\ce{C=O}$ π system via a tetrahedral … D. Imine. M. Tokunaga, A. Hamasaki, in Comprehensive Chirality, 2012. Like the amines, once again the stoichiometric quantity of anhydride as calculated by the following equation may not provide the optimum production value with a commercial epoxy resin: Owing to the fact that the anhydride can undergo a competing chemical reaction with any hydroxyl group present, experience has shown that the preferred value determined by experiment is usually around 85–100% of the calculated theoretical stoichiometry. The development of ‘living’ and ‘alternating’ natures when using aluminum porphyrin as a catalyst, coupled with a quaternary organic salt (Q+Y−), is due to the formation of a six-coordinate aluminum porphyrin (7), in which the reaction proceeds on both sides of the aluminum porphyrin plane (equation 4)5. Namely, Yoshinaga et al. reported a kinetic resolution of secondary alcohols by acylation with vinyl acetate but the selectivity was moderate.20c Kano et al.

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