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A Computational Study of the Intramolec­ular Carbolithiation of Aryllithiums: Solvent and Substituent Effects

Abstract : The intramolecular carbolithiation of olefinic aryllithiums provides an interesting route to functionalized carbo- and heterocyclic systems. We have computed mechanistic energy profiles (DFT) by varying the nature of the solvent and aryllithium. Our calculations suggest that the solvent mainly impacts the aggregation state of the aryllithium intermediates rather than activates the reactive species themselves. Further investigations revealed that substitution of the terminal position of the double bond and the N-allyl side-chain strongly influence the energy barriers, in good agreement with experimental data.
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https://hal.archives-ouvertes.fr/hal-01450750
Contributor : Paola Nava Connect in order to contact the contributor
Submitted on : Tuesday, January 31, 2017 - 12:45:38 PM
Last modification on : Tuesday, December 14, 2021 - 4:45:45 PM

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Jean-Marc Mattalia, Paola Nava. A Computational Study of the Intramolec­ular Carbolithiation of Aryllithiums: Solvent and Substituent Effects. European Journal of Organic Chemistry, 2016, 2016 (2), pp.394 - 401. ⟨10.1002/ejoc.201501208⟩. ⟨hal-01450750⟩

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