Artículo
Nudelman, N.S.; Vazquez, A. "Solvent and ligand effects on the tandem addition-lithiation-electrophilic substitution of phenyllithium on αβ-unsaturated carbonyl compounds" (2005) International Journal of Molecular Sciences. 6(1-2):97-103
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Abstract:
The reaction of phenyllithium with E-cinnamaldehyde is extremely sensitive to the reaction conditions and surprising changes in the product distribution were observed upon changes in the solvent, concentrations, duration or temperature of the reaction. For these reasons the above mentioned reaction was considered an appropriate model to examine solvent and aggregation effects of PhLi. On the other hand, when two or trhee equiv of phenyllithium are used, instead of one, the reaction transforms into a surprising tandem addition-lithiation-β-alkylation sequence, that can be successfully applied to the synthesis of substituted dihydrochalcones. The observed effects upon changes in the reaction conditions, as well as the effects of additives that modify the PhLi dimer-monomer equilibrium are consistent with a reaction pathway in which dimeric phenyl lithium attacks to the E-cinnamaldehyde without previous deaggregation. Usually, monomers are found to be more reactive than dimers, but, in this reaction the opposite effect is observed, and the tandem reaction spectacularly decreases with the (PhLi) 2 concentration. © 2005 by MDPI.
Registro:
| Documento: | Artículo |
| Título: | Solvent and ligand effects on the tandem addition-lithiation-electrophilic substitution of phenyllithium on αβ-unsaturated carbonyl compounds |
| Autor: | Nudelman, N.S.; Vazquez, A. |
| Filiación: | Department of Organic Chemistry, Facultad de Ciencias Exactas, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina |
| Palabras clave: | Aggregates; Chalcones; Cinnamaldehyde; Phenyllithium; Tandem reactions; carbonyl derivative; chalcone derivative; cinnamaldehyde; lithium derivative; phenyllithium; unclassified drug; addition reaction; article; concentration response; lithiation; reaction analysis; substitution reaction; synthesis; temperature sensitivity |
| Año: | 2005 |
| Volumen: | 6 |
| Número: | 1-2 |
| Página de inicio: | 97 |
| Página de fin: | 103 |
| Título revista: | International Journal of Molecular Sciences |
| Título revista abreviado: | Int. J. Mol. Sci. |
| ISSN: | 14220067 |
| CAS: | cinnamaldehyde, 104-55-2 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14220067_v6_n1-2_p97_Nudelman |
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Citas:
---------- APA ----------
Nudelman, N.S. & Vazquez, A. (2005) . Solvent and ligand effects on the tandem addition-lithiation-electrophilic substitution of phenyllithium on αβ-unsaturated carbonyl compounds. International Journal of Molecular Sciences, 6(1-2), 97-103.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14220067_v6_n1-2_p97_Nudelman [ ]
---------- CHICAGO ----------
Nudelman, N.S., Vazquez, A. "Solvent and ligand effects on the tandem addition-lithiation-electrophilic substitution of phenyllithium on αβ-unsaturated carbonyl compounds" . International Journal of Molecular Sciences 6, no. 1-2 (2005) : 97-103.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14220067_v6_n1-2_p97_Nudelman [ ]
---------- MLA ----------
Nudelman, N.S., Vazquez, A. "Solvent and ligand effects on the tandem addition-lithiation-electrophilic substitution of phenyllithium on αβ-unsaturated carbonyl compounds" . International Journal of Molecular Sciences, vol. 6, no. 1-2, 2005, pp. 97-103.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14220067_v6_n1-2_p97_Nudelman [ ]
---------- VANCOUVER ----------
Nudelman, N.S., Vazquez, A. Solvent and ligand effects on the tandem addition-lithiation-electrophilic substitution of phenyllithium on αβ-unsaturated carbonyl compounds. Int. J. Mol. Sci. 2005;6(1-2):97-103.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14220067_v6_n1-2_p97_Nudelman [ ]
