Beiträge zur Furanchemie I

Moldenhauer, Otto; Trautmann, Günter; Irion, Wilhelm; Pfluger, Richard; Döser, Helene; Mastaglio, Dominik; Marwitz, Heinrich

doi:10.1002/jlac.19535800302

Cited by 21 publications

(6 citation statements)

References 23 publications

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“…The latter was oxidised with nitric acid to afford dimethyl 2,5-furandicarboxylate, which, after the alkaline hydrolysis gave FDCA in 50% yield. (Scheme 28) It has been suggested 145,207,211 that the reaction is more convenient and efficient when 5-chloromethylfuroate is converted into methyl 5-acylmethyl-2-furoate 66 and the latter was oxidised to 2,5-furandicarboxylate. But according to my observation, it prolongs the time of the reaction and does not improve the yield much.…”

Section: Scheme 27mentioning

confidence: 99%

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Lewkowski

2003

ChemInform

118

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Section: Scheme 27mentioning

confidence: 99%

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Lewkowski

2003

ChemInform

118

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“…Another drawback of the Blanc reaction is that the product is an extremely potent allergen.) 18 Subsequently, oxidation is required in order to transform this intermediate into product 2,5-FDCA. 19 A more attractive synthetic approach for the conversion of 2-furoic acid into 2,5-FDCA is based on the well-known Henkel reaction (also called Raecke/Henkel process) (Scheme 1, route 3a).…”

Section: Introductionmentioning

confidence: 99%

Concurrent formation of furan-2,5- and furan-2,4-dicarboxylic acid: unexpected aspects of the Henkel reaction

et al. 2013

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The concurrent formation of furan-2,5-and furan-2,4-dicarboxylic acid under solvent free conditions via a disproportionation reaction is described. By reacting potassium-2-furoate at 260 uC in the presence of 22 mol% of (Lewis acidic) catalysts like CdI 2 or ZnCl 2 , potassium-2-furoate is disproportionated to furan and furandicarboxylic acids. Besides furan and furan-2,5-dicarboxylic acid (2,5-FDCA) as the main products, furan-2,4-dicarboxylic acid (2,4-FDCA) is also formed as a by-product. Experimental evidence has been obtained that, under the reaction conditions applied, 2,5-FDCA and 2,4-FDCA are formed by separate reaction pathways. Selectivity towards the different FDCA isomers is affected by the type of catalyst used.Single-crystal X-ray analysis shows that 2,4-FDCA has a more 'linear' character compared to 2,5-FDCA and hence is structurally more comparable to terephthalic acid (TA), making it an interesting monomer for synthetic polyesters.3 Electronic supplementary information (ESI) available: 1 H-NMR spectra of potassium 2-furoate, 2,5-furandicarboxylic acid and 2,4-furandicarboxylic acid, Relative ratio of 2,5-FDCA and 2,4-FDCA formation over time according to 1 H-NMR. CCDC 907968. For ESI and crystallographic data in CIF or other electronic format see Scheme 4 Schematic representation of the synthesis of 2,5-FDCA 3a, 2,4-FDCA 3b and its corresponding dimethyl esters 4a,b.15680 | RSC Adv.,

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“…Mass spectra were recorded on a Varian CH 7A, and high-resolution mass spectra (HRMS) on a Varian MAT 711 spectrometer. The following substrates were prepared according to literature procedures: 2-bromobenzophenone (4c), 40 2bromobenzoylferrocene (14), 41 ethyl 5-bromo-2-furoate (4f), 42 diethyl 4-bromoisophthalate (4d), 43 2,4-dibromo-1-iodobenzene 44 and tri-n-butyltinferrocene. 31 equiv), CoCl 2 (5.0 mol%) and Et 2 O (3.0 mL).…”

Section: -Fluorobenzophenonementioning

confidence: 99%

Cobalt-Catalyzed Cross-Coupling Reactions of Heterocyclic Chlorides with Arylmagnesium Halides and of Polyfunctionalized Arylcopper Reagents with Aryl Bromides, Chlorides, Fluorides and Tosylates

Knöchel¹,

Korn²,

Schade³

et al. 2006

Synthesis

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A range of aromatic organocopper or organomagnesium compounds undergo smooth cross-coupling reactions with aryl bromides, chlorides, fluorides and tosylates, leading to polyfunctionalized aromatics or heterocycles in the presence of cobalt salts (5-7.5 mol%) as catalysts. Very mild reaction conditions are needed and, in the case of cross-coupling with organocopper compounds, Bu 4 NI (1 equiv) and 4-fluorostyrene (20 mol%) are essential as promoters for successful couplings.

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Beiträge zur Furanchemie I

Cited by 21 publications

References 23 publications

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Concurrent formation of furan-2,5- and furan-2,4-dicarboxylic acid: unexpected aspects of the Henkel reaction

Cobalt-Catalyzed Cross-Coupling Reactions of Heterocyclic Chlorides with Arylmagnesium Halides and of Polyfunctionalized Arylcopper Reagents with Aryl Bromides, Chlorides, Fluorides and Tosylates

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