A convenient synthesis of olefins via deacylation reaction |
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| Authors: | Shogo Nakatsu Vakhid A Mamedov |
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| Affiliation: | a Department of Environmental Chemistry and Materials, Faculty of Environmental Science and Technology, Okayama University, Tsushima Okayama 700-8530, Japan
b A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Science, Arbuzov str. 8, Kazan 420088, Russian Federation |
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| Abstract: | A convenient and environmentally-friendly synthetic method of olefins via deacylation reaction is described. The reaction gives olefins by condensation of aldehydes with a variety of 1,3-dicarbonyl compounds in the presence of anhydrous potassium carbonate at room temperature in high yields (70-90%) in one step. The synthetic potential of this strategy can be used as an alternative procedure to the Wittig, Wittig-Horner reactions. The stereochemistry of the resulted olefins was determined by NOE experiment with correct radio frequency and X-ray analysis. The E/Z selectivity of the deacylation reaction depends on the α-substituents of the 1,3-dicarbonyl compounds. |
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| Keywords: | Wittig reaction Wittig-Horner reactions Aldehydes Unsaturated esters |
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