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Abstract:

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.

Registro:

Documento: Artículo
Título:A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies
Autor:Nudelman, N.S.; Schulz, H.G.
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428, Buenos Aires, Argentina
Año:1999
Número:12
Página de inicio:2761
Página de fin:2767
DOI: http://dx.doi.org/10.1039/a904635f
Título revista:Journal of the Chemical Society. Perkin Transactions 2
Título revista abreviado:J Chem Soc Perkin Trans 2
ISSN:03009580
CODEN:JCPKB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n12_p2761_Nudelman

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Citas:

---------- APA ----------
Nudelman, N.S. & Schulz, H.G. (1999) . A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies. Journal of the Chemical Society. Perkin Transactions 2(12), 2761-2767.
http://dx.doi.org/10.1039/a904635f
---------- CHICAGO ----------
Nudelman, N.S., Schulz, H.G. "A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies" . Journal of the Chemical Society. Perkin Transactions 2, no. 12 (1999) : 2761-2767.
http://dx.doi.org/10.1039/a904635f
---------- MLA ----------
Nudelman, N.S., Schulz, H.G. "A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies" . Journal of the Chemical Society. Perkin Transactions 2, no. 12, 1999, pp. 2761-2767.
http://dx.doi.org/10.1039/a904635f
---------- VANCOUVER ----------
Nudelman, N.S., Schulz, H.G. A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies. J Chem Soc Perkin Trans 2. 1999(12):2761-2767.
http://dx.doi.org/10.1039/a904635f