Regioselective ring opening of alkylidenecyclopropanone silyl acetals |
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| Authors: | Morifumi Fujita |
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| Affiliation: | Graduate School of Material Science, Himeji Institute of Technology, University of Hyogo, Kamigori, Hyogo 678-1297, Japan |
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| Abstract: | Alkylidenecyclopropanone silyl acetals are readily available from the reaction of an alkylidenemethyliodonium salt and ketene silyl acetals in the presence of triethylamine. The three different C-C bonds of the cyclopropane ring can be selectively cleaved with HCl, Lewis acid, or fluoride. The alkylideneallyl cation formed via the cleavage of C2-C3 bond with Lewis acids shows further selectivity in reacting with a nucleophile. |
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| Keywords: | Alkylidenecyclopropane Allyl cation Alkylidenecarbene Iodonium salt |
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