Réaction du diméthylcuprate de lithium avec les dérivés carbonylés α,β-insaturés α-fluorés et α-chlorés |
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Authors: | C Chuit R Sauvêitre D Masure JF Normant |
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Institution: | Laboratoire de Chimie des Organoéléments, Tour 44, 2e étage, 4 Place Jussieu, 75230 Paris Cedex 05, France |
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Abstract: | Depending on the nature of the halogen, α-fluoro- and α-chloro-α,β-unsaturated carbonyl compounds (whose reduction potentials are greater than ? 2.4V) react in different ways with lithium dimethylcuprate. With α-fluoro derivatives, both 1,2- and 1,4-addition is observed, their ratios depend on the steric hindrance of the β-position. 1,4-Addition products are obtained from aldehydes and β-monosubstituted α-chloro-α,β-ethylenic ketones and esters. β,β-Disubstituted α-chloro ketones and esters give only reduction of halogen via halogen-metal exchange. |
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