Dichlorotris(triphenylphosphine)ruthenium(II) catalyzed dehydrogenation of some natural products using cyclohexanone as acceptor

Add time:08/31/2019    Source:sciencedirect.com

Cyclohexanone has been used as an acceptor for the dehydrogenation of some natural products in the presence of RuCl2(PPh3)3. Only menthol undergoes appreciable dehydrogenation when compared to cholesterol and β-citronellol. Menthone, cholest-4-en-3-one and cholest-1,4-diene-3-one and citronellal are the products from these compounds. When carbohydrates are used as donors, in most cases the corresponding lactones are formed. The ratio of acceptor to donor is maintained at 6 in the latter cases to avoid disproportionation of the carbohydrates. Acids, isomer and epimer are formed in certain cases. It is observed that the dehydrogenation of carbohydrates is increased at elevated temperatures. The susceptibility to dehydrogenation of the carbohydrates is in the order sorbitol > mannitol > L-arabinose ≈ D-xylose > D-glucose ≈ sucrose > D-mannose ≈ D-galactose.

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