Novel and efficient approach to (Z)-4-trifluoroethylidene-1,3-dioxolane derivatives via (trifluoromethyl)ethynylation of ketones and aldehydes |
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Authors: | Sung Lan Jeon Jung Ah Cho In Howa Jeong |
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Affiliation: | a Department of Chemistry, Yonsei University, Wonju, Republic of Korea b Korea Research Institute of Chemical Technology, Daejeon, Republic of Korea |
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Abstract: | Perfluoroalkylated 4-trifluoroethylidene-1,3-dioxolanes 2a-p were prepared in quantitative yields from the reaction of new stable (trifluoromethyl)ethynylation reagent 1a with TBAF at −15 °C for 10 min, followed by treatment with phenyl perfluoroalkylated ketones at room temperature. The use of aldehydes under the same reaction condition afforded 1,3-dioxolanes 2q-r in good yields. The reaction of 1a with TBAF, followed by treatment with aldehydes or ketones at −15 °C for 10 min and then with trifluoroacetophenone at room temperature provided 1,3-dioxolane derivatives 2s-t in good yields. Tetrabutylammonium trifluoropropynylide [II] was treated with benzaldehyde derivatives at −15 °C for 10 min, followed by treatment with trifluoroacetophenone, to give the corresponding 1,3-dioxolanes 2u-z and 1,3-dioxines 3u-z with different reaction condition. |
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Keywords: | 4-Trifluoroethylidene-1,3-dioxolanes (Trifluoromethyl)ethynylation Perfluoroalkylated ketones Aldehydes 4-Trifluoroethylidene-4H-1,3-dioxines TBAF |
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