Carbanion addition to a metalated acetaldehyde. A new regiospecific alkene synthesis |
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| Institution: | 1. Department of Chemical Physiology and Biochemistry, School of Medicine, Oregon Health & Science University, 3181 SW Sam Jackson Park Road, Portland, Oregon 97239, USA;2. Department of Chemistry, University of Central Florida, 4111 Libra Drive, Orlando, FL 32816, USA |
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| Abstract: | The reaction of 2-(dicarbonyl)(η5-cyclopentadienyl)iron]acetaldehyde with organolithium and Grignard reagents results in efficient addition to the aldehyde carbonyl. The intermediate alkoxides have been treated with tetrafluoroboric acid to give high yields of isolated η2-alkene complexes of the dicarbonyl(η5-cyclopentadienyl)iron cation. Using this procedure the following alkenes were produced as complexed ligands to iron in 50–90% yield: propene, 1-hexene, 3-methyl-1-pentene, 3,3-dimethyl-1-butene, 1,3-butadiene, and styrene. |
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