Cyclodextrins containing an acetone bridge. Synthesis and study as epoxidation catalysts |
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Authors: | Rousseau Cyril Christensen Brian Petersen Torben Ellebaek Bols Mikael |
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Affiliation: | Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000, Aarhus, Denmark. |
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Abstract: | Three cyclodextrine derivatives (6A,6D-di-O-(prop-2-one-1,3-dienyl)-alpha-cyclodextrin (1), 6-O-(prop-2-one-1-yl)-alpha-cyclodextrin (2) and 6A,6D-di-O-(prop-2-one-1,3-dienyl)-beta-cyclodextrin (3)) were synthesised and investigated as epoxidation catalysts. The three compounds were synthesised from the corresponding perbenzylated cyclodextrins which were mono- or didebenzylated in the 6-position using Sina?'s method. Reaction with NaH and methallyl chloride in the case of 2, or methallyl dichloride in the case of 1 and 3, followed by dihydroxylation, periodate cleavage and protection group removal gave the target compounds. All three compounds catalysed, in the presence of oxone, the epoxidation of a series of alkenes. Epoxidation was compared to the reaction catalysed by simple ketones and inhibition was studied. |
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