Decarbonylation and dehydrogenation of carbohydrates

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549503, 568853, 568863, C07D30702

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active

H00009180

ABSTRACT:
Carbohydrates, especially aldose or ketose sugars, including those whose carbonyl group is masked by hemi-acetal or hemi-ketal formation, are decarbonylated by heating the feed carbohydrate together with a transition metal complex in a suitable solvent. Also, primary alcohols, including sugar alditols are simultaneously dehydrogenated and decarbonylated by heating a mixture of rhodium and ruthenium complexes and the alcohol and optionally a hydrogen acceptor in an acceptable solvent. Such defarbonylation and/or dehydrogenation of sugars provides a convenient procedure for the synthesis of certain carbohydrates and may provide a means for the conversion of biomass into useful products.

REFERENCES:
patent: Re32084 (1986-02-01), Hoetz
patent: 4089871 (1978-05-01), Lillwitz
patent: 4197414 (1980-04-01), Hartwell et al.
patent: 4433184 (1984-02-01), Huibers et al.
patent: 4487980 (1984-12-01), Arena
patent: 4540836 (1985-09-01), Fenton
Y. Nakamura, et al., Bull. Chem. Soc., Jpn., "The Dehydration of D-Fructose to 5-Hydroxymethyl-2-Furaldehyde," 53, 3705-3706, (1980).
P. Collins, Chem. Communications, "Photochemically Induced Ring Contraction, a Furanoid Ring from a Pyranosidulose," pp. 403-405 (1968).
S. Rajagopal, et al., J. Mol. Cat., "Deactivation of RuCl.sub.2 (PPh.sub.3).sub.3 during Disproportination of D-Glucose in Amide Solvents," 22, pp. 131-135 (1983).
W. M. Kruse, et al., Carbohyd. Res., "Homogeneous Catalytic Hydrogenation of Sugars," 64, pp. 293-296 (1978).
R. Whistler, et al., J. Org. Chem., "Photolysis of Penta-O-Acetyl-Aldehyde-D-Glucose," 36(17), pp. 2575-2576, (1971).
S. Pillari, et al., J. Mol. Cat., "Dichlorotris(Triphenylphosphine) Ruthenium (II) Catalyzed Dehydrogenation . . . ," 16, pp. 349-358, (1982).
D. Ward, et al., Chemistry and Industry, "Decarbonylation of Aldehyde Sugar Derivative . . . " pp. 162-163, (1976).
Chemical Abstracts, 93: 26260e, "Hydroxymethylfurfuryl" (1980).
K. Kaneda, et al., Chemistry Letters, "Decarbonylation of .alpha. & .beta.-Diketones Catalyzed by Rhodium Compounds," pp. 215-216 (1974).
Domazeti's, J. Chem. Comm., "Catalytic Decarbonylation of Aldehydes . . . ," pp. 939-940, (1980).
K. Ohno, et al., J. Am. Chem. Soc., "Organic Snythesis by Means of Noble Metal Compounds," 90(1), pp. 99-107, (1968).
S. Maple, et al., J. Am. Chem. Soc., "Detailed Tautomeric Equilibrium of Aqueous D-Glucose," 109, pp. 3168-3169 (1987).
M. MacCoss, et al., Tetrahedron Letters, "Synthesis of All Four Possible Isomers of the Acyclonacleoside . . . ," 26(36), pp. 4287-4290 (1985).
M. Baird, et al., J. Chem. Soc. (A), "The Decarbonylation of Aldehydes by . . . ," pp. 348-351 (1968).
D. Doughty, et al., J. Am. Chem. Soc., "Catalytic Decarboylation of Aldehydes," 100(22), pp. 7083-7085, (1978).
L. Lillwitz, Chemical Abstracts: 89: 129386x, "Furfuryl Alcohol," (1978).

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