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Abstract:

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.

Registro:

Documento: Artículo
Título:The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
Autor:Vázquez, A.J.; Nudelman, N.S.
Filiación:Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pab. II, P. 3, 1428 Buenos Aires, Argentina
Palabras clave:Addition to α,β-unsaturated compounds; Additives; Aggregation states; Ligands; Phenyllithium; Tandem reactions
Año:2005
Volumen:2005
Número:12
Página de inicio:332
Página de fin:340
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:14246376
PDF:https://bibliotecadigital.exactas.uba.ar/download/paper/paper_14246376_v2005_n12_p332_Vazquez.pdf
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez

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Citas:

---------- APA ----------
Vázquez, A.J. & Nudelman, N.S. (2005) . The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF. Arkivoc, 2005(12), 332-340.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez [ ]
---------- CHICAGO ----------
Vázquez, A.J., Nudelman, N.S. "The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF" . Arkivoc 2005, no. 12 (2005) : 332-340.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez [ ]
---------- MLA ----------
Vázquez, A.J., Nudelman, N.S. "The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF" . Arkivoc, vol. 2005, no. 12, 2005, pp. 332-340.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez [ ]
---------- VANCOUVER ----------
Vázquez, A.J., Nudelman, N.S. The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF. Arkivoc. 2005;2005(12):332-340.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p332_Vazquez [ ]