This is a pdf file of an unedited manuscript that has. Epoxidation of 2 with tbuooh in the presence of vanadyl acetylacetonate voacac 2 as catalyst furnished epoxide 19 in a stereospecific reaction 35,42 44. It is used in organic chemistry as a catalyst for the epoxidation of allylic alcohols by. The interest in the chemistry of oxovanadium complexes has. Vanadyliv complexes of ferulic and cinnamic acid with quinic acid 1,2. Pdf synthesis, molecular structure and properties of oxo. Vanadyl acetoneacetate is not optically active, so there is no stereochemistry to consider. Vanadyl acetylacetonate is one of numerous organometallic compounds also known as metalorganic, organoinorganic and metalloorganic compounds sold by american elements under the trade name ae organometallics for uses requiring nonaqueous solubility such as recent solar energy and water treatment applications. Stereochemistry of uranyl acetylacetonate hydrate 147 comyns et al.
Sodium acetylacetonate is a sodium source that is soluble in organic solvents as an organometallic compound also known as metalorganic, organoinorganic and metalloorganic compounds. Vanadyl acetylacetonate, or oxobis2, 4pentanedionovanadiumiv by the iupac naming system, is a deep blue crystal with several applications beyond the scope of this experiment. Acetylacetonate forms neutral complexes with most metals. The spectra have been analyzed and the components of the g tensor and of the vanadium hyperfine interaction tensors have been determined, and for the porphyrin the nitrogen extrahyperfine interaction tensor has been obtained. Electron paramagnetic resonance study of intermolecular exchange coupling in an undiluted vanadyl complex. Vox mixedoxide supported sba15 catalysts were prepared by the molecular designed dispersion method mdd using acetylacetonate complexes. Vanadyl acetylacetonate v69 3153262 c 10 h 14 o 5 v spectrum chemical important update all sales after march 2, 2020 are final and nonreturnable for covid19 related items. Definition of vanadyl acetylacetonate in the dictionary. Structure in the electronic spectra of vanadyl acetylacetonate. Yet, i havent been able to find anything about the characteristics of a typical vo ir spectrum. New mechanism for the reduction of vanadyl acetylacetonate to. Kinetics of oxidation of vanadyl acetylacetonate by oxygen in.
Stereoselective reactions of alkenes massey university. The reaction, which is pseudo firstorder with respect to voacac2 and o2, is inhibited by hacac and a vanadiumv complex. Abstract in this study, a new mechanism for the reduction of vanadyl acetylacetonate, voacac2, to vanadium acetylacetonate, vacac3. Ir spectral analysis of oxovanadium acetylacetone biology essay. Vanadiumcatalyzed epoxidation of cyclic allylic alcohols. Material safety data sheet toxin and toxintarget database. Chapter 5 118 program and recorded images were integrated and scaled using saintbruker. In the procedures right at the begining it says add 2. Vanadylivacetylacetonatewuxi zhanwang chemical reagent. However, acetylacetonate is a stronger ligand that displaces the water molecules. Vanadyl acetylacetonate suppliers, manufacturers, cas no 3153. Ultra high purity and high purity forms may be considered.
Information and translations of vanadyl acetylacetonate in the most comprehensive dictionary definitions resource on the web. The molecule is square pyramidal, with idealized c 2v symmetry. Partial oxidation of ethanol on vanadia catalysts on. Controlling nuclearity and stereochemistry in vanadylv and mixed valent v iv v v complexes of oxido. The directing effect of the hydroxyl group within the substrate allows for highly diastereoselective epoxidation of olefins. The bands in the range 4400029000 cm1 are attributed to the n. Stereoselective preparations of epoxy, fluoro and related. The rate data were used to calculate the thermodynamic activation parameters. For working out the oxidation number of vanadium, oxygen counts as 2. Beckman du manual spectrophometer with reflectance attach ment, using.
Manganeseiii acetylacetonate is an one electron oxidant. Acros organics bvba janssen pharmaceuticalaan 3a 2440 geel. Vanadyl acetylacetonate is the chemical compound with the formula voc5h7o22. Our previous work has shown that epoxidation with tbuooh in the presence of vanadyl acetylacetonate voacac2 as a catalyst can be successfully applied to prepare a new family of neoisopulegolbased chiral aminodiol libraries 57. Stereochemistry of uranyl acetylacetonate monohydrate. Continuous wave and pulse epr spectroscopy is employed to determine the location of the voacac2 complexes in the mixedoxide. Catalytic amounts of voacac2 coupled with tbutylhydroperoxide. Voacac 2, vanadiumivoxy acetylacetonate cas number 3153262. Vanadyl acetylacetonate is the chemical compound with the formula voacac2, where acac.
Sigmaaldrich offers a number of vanadyl acetylacetonate products. Thermal decomposition of vanadyl acetylacetonate springerlink. Esr studies and the electronic structure of vanadyl ion. Stereochemistry of epoxidation of some caryophyllenols. Feb 01, 2009 vanadyl acetoneacetate is not optically active, so there is no stereochemistry to consider. Hydroxycinnamic acids are rich in phenolic antioxidants and may reduce the incidence of degenerative diseases, such as cardiovascular disease and cancer, whose mechanism of action is believed to be initiated by free radicals. Controlling nuclearity and stereochemistry in vanadylv. Two different synthesis route depositions are presented to prepare these mixedoxide catalysts in a very controlled way. Voacac2 shows solvatochromism in the selected ionic liquids and behaves as in organic. Reaction of nh 4 vo 3 with the protoligands h 2 l gave the dinuclear complexes lovovol. Ac199590000, ac199590010, ac199590500, ac199592500 synonyms. Located in yixing city a tourist city at the bank side of scenic taihu lake, wuxi zhanwang chemical reagent co.
The electron spin resonance spectra of vanadyl acetylacetonate voacac 2 and a number of its adducts have been examined in benzene solution at ambient temperatures. The esr spectra of vanadyl acetylacetonate and tetraphenylporphyrin have been studied in various liquid solvents and frozen glasses. Vanadyl acety lacetonate, voacac 2, is used as a precursor. Vanadyl acetylacetonate 3153262 v69 spectrum chemical. The stereochemistry of vanadyl acetylacetonate catalyzed epoxidation of cyclic allylic alcohols with tcrfbutyl hy droperoxide is examined and. Epoxidation of methyl shode 7 gave 8 45 mg, 43% and 9 44 mg, 43%.
Pdf the complex voodaho oda ochcoo has been obtained by reaction of aqueous solutions of voacac with oxydiacetic acid. It is a bluegreen solid that dissolves in polar organic solvents. The vanadiumcatalyzed epoxidation reaction voacac2tbutyl. Nov 22, 2018 controlling nuclearity and stereochemistry in vanadylv and mixed valent v iv v v complexes of oxido. Epoxidations with tertbutyl hydroperoxidevanadyl acetylacetonate vanadyl acetylacetonate 19 mg, 0. Vanadyl acetylacetonate is the chemical compound with the formula voacac 2, where acac is the conjugate base of acetylacetone.
The acac anion can act as a ligand towards metal ions, typically forming a bidentate complex where the metal is bound to the two oxygen atoms, thus forming a 6membered ring. The structure of manganeseiii acetylacetonate is shown as below. We report the structural characterization of vanadyl acetylacetonate in imidazolium room. Vanadyl acetylacetonate filled pvdf membranes as the core of. Ketoenol equilibrium of acetylacetone and formation of acetylacetonate anion. Use the link below to share a fulltext version of this article with your friends and colleagues. It is generally immediately available in most volumes. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. Vanadyl ir stretching writing a lab report for inorganic and i have to comment on how the different ligands affect the vo stretching in two different complexes. Synopsis derivatives of the tridentate 2,6pyridinedimethanol ligand were reacted with nh 4 vo 3 or voacac 2 acac acetylacetonate.
A recent study used this compound to catalyze stereoselective synthesis of. Each calcination step was performed in a quartz rotary furnace under 50 mlmin. The vanadyl acetylacetonate was chosen as the v 2 o 5 precursor since it decomposes in air at relatively low temperature about 400 c with formation of vanadiumv oxide 20, 21. However, upon applying this condition with 3, methylenebutyrolactone 4 was observed as the major product. Mononuclear anionic species vo 2 l, which were isolated as alkaline. Formation of trans epoxides by syn epoxidation is a consequence of the conformational flexibility of the ninemembered ring, which places. Ortolano, thomas russell, spectral studies on vanadyl complexes. Stereoselective voacac2 catalyzed epoxidation of acyclic. This complex features the vanadyliv group, and many related compounds are known. Stereoselective synthesis and investigation of isopulegol. Preparation of polymeric membranes with and without the catalyst. Vanadyl acetylacetonate is a blue complex with the formula voacac 2. The kinetics of oxidation of vanadyl acetylacetonate to voohomeacac by molecular o2 in meoh have been studied spectrophotometrically.
Pdf thermal decomposition of vanadyl acetylacetonate. Structural characterization and dft study of vivoacac2 in. Compounds 1, 3, 8, 9 and 10 were prepared via their benzoyl. An international journal for rapid communication of synthetic organic chemistry.
The complex catalyzes epoxidation of allylic alcohols by peroxides. Vanadyl acetylacetonate voacac 2 is used as a catalyst for epoxidation of allylic alcohols with the use of tertbutyl hydroperoxide as the reoxidant. This complex features the vanadyl iv group, and many related compounds are known. Raman measurements were performed using a horibajobin yvon confocal labram raman microscope utilizing a 633 nm exci. Vanadyl acetylacetonate, voacac 2, is the simplest. Epoxidation of the caryophyllene allylic alcohols 3. Stereochemistry of epoxidation of some caryophyllenols the. Preparation of vanadyl acetylacetonate voacac2py the. Since our earlier results clearly demonstrated that substituents at nitrogen of aminodiols exerted definite influence on the efficiency. Insitu fourier transform infrared spectroscopy gas phase studies of vanadium iv oxide coating by atmospheric pressure chemical vapour deposition using vanadyl iv acetylacetonate, thin solid films, 2008, vol. Preparation and characterisation of metal acetylacetonate. Structural investigation of vanadylacetylacetonate. The reaction with a vanadyl reagent results in higher stereoselectivity as it bonds chelates to the oxygen 7 oh reagent oh o reagent.
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