The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF

The effect of donor ligands, usually expected to enhance the reactivity of organolithiums, was studied on the addition of PhLi to E-cinnamaldehyde in THF, under conditions that lead the reaction toward the production of 1,3-diphenylpropanone. It was observed that in the presence of TMEDA and HMPT, t...

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Detalles Bibliográficos
Autor principal: Vázquez, Alvaro Joaquín
Publicado: 2005
Materias:
Addition to α,β-unsaturated compounds
Additives
Aggregation states
Ligands
Phenyllithium
Tandem reactions
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p332_Vazquez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_14246376_v2005_n12_p332_Vazquez
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spelling paper:paper_14246376_v2005_n12_p332_Vazquez2023-06-08T16:13:57Z The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF Vázquez, Alvaro Joaquín Addition to α,β-unsaturated compounds Additives Aggregation states Ligands Phenyllithium Tandem reactions The effect of donor ligands, usually expected to enhance the reactivity of organolithiums, was studied on the addition of PhLi to E-cinnamaldehyde in THF, under conditions that lead the reaction toward the production of 1,3-diphenylpropanone. It was observed that in the presence of TMEDA and HMPT, the rate of that reaction becomes slower than in the absence of ligands; the effect of HMPA was even more spectacular, at concentration [HMPA]: [PhLi] ≥ 4 the reaction becomes almost completely inhibited. These results show the complexity of solvation effects on the reactions of organolithiums and how substrate-reagent-ligand-solvent interactions are usually specific for the system under study. © ARKAT. Fil:Vázquez, A.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2005 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p332_Vazquez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Addition to α,β-unsaturated compounds
Additives
Aggregation states
Ligands
Phenyllithium
Tandem reactions
spellingShingle Addition to α,β-unsaturated compounds
Additives
Aggregation states
Ligands
Phenyllithium
Tandem reactions
Vázquez, Alvaro Joaquín
The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
topic_facet Addition to α,β-unsaturated compounds
Additives
Aggregation states
Ligands
Phenyllithium
Tandem reactions
description The effect of donor ligands, usually expected to enhance the reactivity of organolithiums, was studied on the addition of PhLi to E-cinnamaldehyde in THF, under conditions that lead the reaction toward the production of 1,3-diphenylpropanone. It was observed that in the presence of TMEDA and HMPT, the rate of that reaction becomes slower than in the absence of ligands; the effect of HMPA was even more spectacular, at concentration [HMPA]: [PhLi] ≥ 4 the reaction becomes almost completely inhibited. These results show the complexity of solvation effects on the reactions of organolithiums and how substrate-reagent-ligand-solvent interactions are usually specific for the system under study. © ARKAT.
author Vázquez, Alvaro Joaquín
author_facet Vázquez, Alvaro Joaquín
author_sort Vázquez, Alvaro Joaquín
title The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
title_short The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
title_full The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
title_fullStr The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
title_full_unstemmed The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
title_sort unexpected effects of added ligands on the addition of phenyllithium to e-cinnamaldehyde in thf
publishDate 2005
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p332_Vazquez
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