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Abstract:

The kinetics of benzil reduction by lithium metal in THF were investigated under different reaction conditions. The main reaction products were phenylacetophenone and bibenzyl; 1,2-diphenylethanol and diphenylethene were minor products. The first radical anion intermediate formed by electron transfer upon chemisorption of the benzyl on the metal surface was fully characterized and quantitatively determined by ESR spectroscopy. The kinetics of the benzil decay and of the formation of the two main products were followed by GC and ESR. A unique feature of this reaction is the presence of a well-defined and reproducible induction period. A mechanism is proposed which accounts for the main experimental observations. Copyright © 2003 John Wiley & Sons, Ltd.

Registro:

Documento: Artículo
Título:Reaction of lithium metal with benzil in THF. A kinetic study
Autor:Nudelman, N.S.; Velurtas, S.; Grela, M.A.
Filiación:Dpto. Química Orgánica, Facultad de Ciencias Exactes, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Dpto. de Química, Facultad de Ciencias Exactes, Univ. Nacional de Mar del Plata, B7602AYL Mar del Plata (BA), Argentina
Palabras clave:Benzil; Heterogenous systems; Induction period; Lithium metal; Organolithium; Surface reactions; Electron spin resonance spectroscopy; Electrons; Organic compounds; Reaction kinetics; Induction periods; Lithium
Año:2003
Volumen:16
Número:10
Página de inicio:669
Página de fin:674
DOI: http://dx.doi.org/10.1002/poc.649
Título revista:Journal of Physical Organic Chemistry
Título revista abreviado:J Phys Org Chem
ISSN:08943230
CODEN:JPOCE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v16_n10_p669_Nudelman

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Citas:

---------- APA ----------
Nudelman, N.S., Velurtas, S. & Grela, M.A. (2003) . Reaction of lithium metal with benzil in THF. A kinetic study. Journal of Physical Organic Chemistry, 16(10), 669-674.
http://dx.doi.org/10.1002/poc.649
---------- CHICAGO ----------
Nudelman, N.S., Velurtas, S., Grela, M.A. "Reaction of lithium metal with benzil in THF. A kinetic study" . Journal of Physical Organic Chemistry 16, no. 10 (2003) : 669-674.
http://dx.doi.org/10.1002/poc.649
---------- MLA ----------
Nudelman, N.S., Velurtas, S., Grela, M.A. "Reaction of lithium metal with benzil in THF. A kinetic study" . Journal of Physical Organic Chemistry, vol. 16, no. 10, 2003, pp. 669-674.
http://dx.doi.org/10.1002/poc.649
---------- VANCOUVER ----------
Nudelman, N.S., Velurtas, S., Grela, M.A. Reaction of lithium metal with benzil in THF. A kinetic study. J Phys Org Chem. 2003;16(10):669-674.
http://dx.doi.org/10.1002/poc.649