Abstract
Abstract The carbonyl-14C kinetic isotope effects and the substituent effects on the reactivity of the Zn-promoted Barbier-type reaction of allyl iodide (3-iodo-1-propene) with benzaldehyde and benzophenone were determined in THF at 25 °C. The observed normal carbon isotope effects as well as positive Hammett ρ values suggest that the reactions go through a direct nucleophilic addition mechanism. No indication of the occurrence of electron transfer was obtained by enone isomerization and dehalogenation probe experiments. Diastereoselectivity in the reaction of crotyl iodide (1-iodo-2-butene) with benzaldehyde was low and independent of the substituent on aldehyde, consistent with the six-membered cyclic transition state.
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