Chlorodimethylaluminum-promoted nucleophilic addition of lithium pentamethylcyclopentadienide to aliphatic aldehydes and DDQ-mediated carbon-carbon bond cleavage of the adducts providing the parent aldehydes |
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Authors: | Minoru Uemura Koichiro Oshima |
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Affiliation: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan |
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Abstract: | Treatment of aliphatic aldehyde with lithium pentamethylcyclopentadienide in the presence of chlorodimethylaluminum provided the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene by the action of a catalytic amount of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). |
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Keywords: | Pentamethylcyclopentadiene Nucleophilic addition Carbon-carbon bond cleavage Chlorodimethylaluminum |
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