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Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde

Jaroslav Horvat ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia
Branimir Klaić ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia
Biserka Metelko ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia
Vitomir Šunjić ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia

Puni tekst: engleski, pdf (6 MB) str. 429-438 preuzimanja: 167* citiraj
APA 6th Edition
Horvat, J., Klaić, B., Metelko, B. i Šunjić, V. (1986). Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde. Croatica Chemica Acta, 59 (2), 429-438. Preuzeto s https://hrcak.srce.hr/177372
MLA 8th Edition
Horvat, Jaroslav, et al. "Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde." Croatica Chemica Acta, vol. 59, br. 2, 1986, str. 429-438. https://hrcak.srce.hr/177372. Citirano 21.04.2021.
Chicago 17th Edition
Horvat, Jaroslav, Branimir Klaić, Biserka Metelko i Vitomir Šunjić. "Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde." Croatica Chemica Acta 59, br. 2 (1986): 429-438. https://hrcak.srce.hr/177372
Harvard
Horvat, J., et al. (1986). 'Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde', Croatica Chemica Acta, 59(2), str. 429-438. Preuzeto s: https://hrcak.srce.hr/177372 (Datum pristupa: 21.04.2021.)
Vancouver
Horvat J, Klaić B, Metelko B, Šunjić V. Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde. Croatica Chemica Acta [Internet]. 1986 [pristupljeno 21.04.2021.];59(2):429-438. Dostupno na: https://hrcak.srce.hr/177372
IEEE
J. Horvat, B. Klaić, B. Metelko i V. Šunjić, "Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde", Croatica Chemica Acta, vol.59, br. 2, str. 429-438, 1986. [Online]. Dostupno na: https://hrcak.srce.hr/177372. [Citirano: 21.04.2021.]

Sažetak
Mechanism of levulinic acid (2) formation in acid catalysed hydrolysis of 2-hydroxymethyl£urane (3) and 5-hydroxymethylfuran- 2-carbaldehyde (1) is studied by 13C-NMR spectroscopy. Hydroxymethyl-derivative of dihydrofurane 5, its anhydro-derivative
6, and an unsaturated keto-aldehyde (8) are determined as intermediates in the transformation of 3 into 2 (Scheme 3). The conversion of 1 into 2 requires more drastic conditions, and
the only two structures determined unambigously are 15 and 16;
the former intermediate led to polymerized material via A-5,
analogous to polymerization of 4 via 13 and 14 (Scheme 4), while
the latter decarbonylates and rearranges to afford levulinic acid
(Scheme 5). Intramolecular oxygen transfer via cyclic intermediates
(Scheme 6), embracing concerted C(l)-O and C(5)-X (X = H or eHO) bond breaking, cannot be proved.

Hrčak ID: 177372

URI
https://hrcak.srce.hr/177372

Posjeta: 346 *