- Catalytic aerobic oxidation of renewable furfural to maleic anhydride and furanone derivatives with their mechanistic studies
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Catalytic transformation of biomass-based furfural to value-added chemicals is an alternative route to the on-going fossil feedstock-based processes. This work describes catalytic aerobic oxidation of furfural to maleic anhydride, an important polymer starting material having a large market with H 5PV2Mo10O40 and Cu(CF 3SO3)2 catalysts. Under the optimized conditions, 54.0% yield of maleic anhydride can be achieved with about 7.5% yield of 5-acetoxyl-2(5H)-furanone formation. Notably, 5-acetoxyl-2(5H)-furanone is a highly value-added, biologically important intermediate that has been applied in pharmaceutical synthesis. The catalytic mechanism for furfural oxidation to maleic anhydride and 5-acetoxyl-2(5H)-furanone has been investigated in detail with identification of several key intermediates. the Partner Organisations 2014.
- Lan, Jihong,Chen, Zhuqi,Lin, Jinchi,Yin, Guochuan
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p. 4351 - 4358
(2014/10/15)
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- Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones
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In this work we report a versatile synthesis of fourteen γ-lactones all structurally related, nine of which are novel compounds, accomplished from the readily available furfural. The phytotoxic activity of the synthesized compounds was evaluated in vitro by the influence on the growth of wheat coleoptiles. The percentages of inhibition were mostly small and not statistically different from control after the third dilution (100 μmol L-1). In general, α,β-unsaturated lactones presented better activities than the saturated ones. The most active compounds presented 51, 68 and 76percent of inhibition in 1000 μmol L-1. The results indicate that regardless of saturation, the presence of the γ-lactone moiety is important for the bioactivity, but their presence has no implications with potency. ?2012 Sociedade Brasileira de Qui?mica.
- Resende, Gabriela C.,Alvarenga, Elson S.,Galindo, Juan C.G.,MacIas, Francisco A.
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p. 2266 - 2270
(2013/04/24)
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- Mass Spectra of Substituted Butenolides
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The mass spectra of a series of substituted butenolides were studied. Their fragmentations in the mass spectrometer strongly depend upon the nature of the substitutents. The fragment's ions include the lactone skeletons, substituents, and resultant derive
- Lin, Shaw-Tao,Kuo, Yueh-Hsiung,Wang, Eng-Chi,Lin, Wen-Chung
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p. 129 - 132
(2007/10/03)
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- Lipase catalyzed enantioselective transesterification of 5-Acyloxy-2(5H)-furanones
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Several lipases catalyse the transesterification of γ-acyloxyfuranones in organic solvents with high enantioselectivities. This method has been used for the kinetic resolution of 5-acetoxy-2(5H)-furanone, 5-acetoxy-4-methyl-2(5H)-furanone and 5-propionyloxy-2(5H)-furanone, in e.e.'s ranging from 68-98%.
- Van Der Deen, Hanneke,Hof, Robert P.,Van Oeveren, Arjan,Feringa, Ben L.,Kellogg, Richard M.
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p. 8441 - 8444
(2007/10/02)
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- HYPERVALENT IODINE OXIDATION: SYNTHESIS OF 5-SUBSTITUTED-2(5H)-FURANONES USING IODOSOBENZENE
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Hypervalent iodine oxidation of 2-(trimethylsilyloxy)furan with iodosobenzene: boron trifluoride etherate in the presence of various nucleophiles yields 5-substituted-2(5H)-furanones.
- Moriarty, Robert M.,Vaid, Radhe K.,Hopkins, Thomas E.,Vaid, Beena K.,Tuncay, Atilla
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p. 3019 - 3022
(2007/10/02)
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- THE SERIES OF SUBSTITUTED BUTANOLIDES AND BUTENOLIDES. V. SYNTHESIS OF 4-HYDROXY-2-BUTEN-4-OLIDE AND ITS DERIVATIVES ON THE BASIS OF THE REACTION OF FURFURAL WITH HYDROGEN PEROXIDE
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New methods were developed for the synthesis of 4-hydroxy-2-buten-4-olide and its derivatives on the basis of the reaction of furfural with hydrogen peroxide in the presence of the compounds of group VI elements and vanadium.The dependence of the yield of 4-hydroxy-2-buten-4-olide on the type of catalyst was established, and the optimum conditions for its production were determined.
- Poskonin, V. V.,Badovskaya, L. A.,Gavrilova, S. P.,Kul'nevich, V. G.
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p. 1535 - 1539
(2007/10/02)
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- Oxidative Substitution Reactions of Organotin Compounds with Lead Tetra-acetate
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A new oxidative substitution reaction where an organotin group is replaced by an acetoxy group has been investigated; this reaction has been successfully applied to the synthesis of 4-ylidenebutenolides.
- Yamamoto, Makoto,Izukawa, Hiroyoshi,Saiki, Masaru,Yamada, Kazutoshi
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p. 560 - 561
(2007/10/02)
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- The Reaction of 2-(Trialkylsiloxy)furans with Lead(IV) Acetate. The Synthesis of dl-Pyrenophorin
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The reaction of 2-(trimethylsiloxy)furans with lead(IV) acetate afforded the corresponding α,β-unsaturated γ-acetoxy-γ-lactones in good yields.The lactones were easily converted into the corresponding 3-acylacrylic acids.Utilizing this reaction, dl-pyrenophorin was synthesized.
- Asaoka, Morio,Yanagida, Noboru,Sugimura, Naoyuki,Takei, Hisashi
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p. 1061 - 1064
(2007/10/02)
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