A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies

The reaction of phenyllithium (in excess) with E-cinnamaldehyde gives a surprising tandem addition β-alkylation, which can be successfully used for the synthesis of substituted dihydrochalcones. The mechanism by which these unexpected reactions could occur is unknown and experimental and theoretical...

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Autores principales: Nudelman, N.S., Schulz, H.G.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_03009580_v_n12_p2761_Nudelman
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_03009580_v_n12_p2761_Nudelman2023-10-03T15:18:06Z A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies Nudelman, N.S. Schulz, H.G. The reaction of phenyllithium (in excess) with E-cinnamaldehyde gives a surprising tandem addition β-alkylation, which can be successfully used for the synthesis of substituted dihydrochalcones. The mechanism by which these unexpected reactions could occur is unknown and experimental and theoretical studies were carried out as a contribution to its understanding. The observed concentration effects, the surprising changes in the product distribution upon changes in the reaction conditions, the haptomeric structure of the calculated intermediates and the calculated activation energies are consistent with a reaction pathway in which dimeric phenyllithium attacks the E-cinnamaldehyde without prior deaggregation. Solvated structures were also calculated using a "dielectric continuum" model for solvent effects. Fil:Schulz, H.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_03009580_v_n12_p2761_Nudelman
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description The reaction of phenyllithium (in excess) with E-cinnamaldehyde gives a surprising tandem addition β-alkylation, which can be successfully used for the synthesis of substituted dihydrochalcones. The mechanism by which these unexpected reactions could occur is unknown and experimental and theoretical studies were carried out as a contribution to its understanding. The observed concentration effects, the surprising changes in the product distribution upon changes in the reaction conditions, the haptomeric structure of the calculated intermediates and the calculated activation energies are consistent with a reaction pathway in which dimeric phenyllithium attacks the E-cinnamaldehyde without prior deaggregation. Solvated structures were also calculated using a "dielectric continuum" model for solvent effects.
format JOUR
author Nudelman, N.S.
Schulz, H.G.
spellingShingle Nudelman, N.S.
Schulz, H.G.
A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies
author_facet Nudelman, N.S.
Schulz, H.G.
author_sort Nudelman, N.S.
title A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies
title_short A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies
title_full A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies
title_fullStr A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies
title_full_unstemmed A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies
title_sort new reaction between e-cinnamaldehyde and phenyllithium. mechanistic studies
url http://hdl.handle.net/20.500.12110/paper_03009580_v_n12_p2761_Nudelman
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