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

Mostrar todas las versiones(3)

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...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Vázquez, A.J., Nudelman, N.S.
Formato: Artículo publishedVersion
Lenguaje:Inglés
Publicado: 2005
Materias:
Addition to α,β-unsaturated compounds
Additives
Aggregation states
Ligands
Phenyllithium
Tandem reactions
Acceso en línea: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 paperaa:paper_14246376_v2005_n12_p332_Vazquez
record_format dspace
spelling paperaa:paper_14246376_v2005_n12_p332_Vazquez2023-06-12T16:50:12Z The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF Arkivoc 2005;2005(12):332-340 Vázquez, A.J. Nudelman, N.S. 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 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion application/pdf eng info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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)
language Inglés
orig_language_str_mv eng
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, A.J.
Nudelman, N.S.
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.
format Artículo
Artículo
publishedVersion
author Vázquez, A.J.
Nudelman, N.S.
author_facet Vázquez, A.J.
Nudelman, N.S.
author_sort Vázquez, A.J.
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 http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p332_Vazquez
work_keys_str_mv AT vazquezaj theunexpectedeffectsofaddedligandsontheadditionofphenyllithiumtoecinnamaldehydeinthf
AT nudelmanns theunexpectedeffectsofaddedligandsontheadditionofphenyllithiumtoecinnamaldehydeinthf
AT vazquezaj unexpectedeffectsofaddedligandsontheadditionofphenyllithiumtoecinnamaldehydeinthf
AT nudelmanns unexpectedeffectsofaddedligandsontheadditionofphenyllithiumtoecinnamaldehydeinthf
_version_ 1769810296645353472

Ejemplares similares