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Abstract:

The reaction of lithium derivatives of aromatic heterocycles with carbon monoxide was studied under several reaction conditions: 2-furyllithium afforded only one product, the tetrahydro-2-furaldehyde (25% yield). On the other hand, 2-thienyllithium and 5-methyl-2-furyllithium gave two and five products, respectively. Although in relatively low yields, formation of highly functionalized compounds takes place in a fast process under mild conditions. For 1,4-dihydroxy-1,4-bis(5-methyl-2-furanyl)butane-2,3-dione, reaction conditions were achieved to obtain this difficult to prepare derivative in 50% yield. To the best of our knowledge, this is the first report on the reaction of lithiated aromatic heterocycles with CO: evidence is given on the involvement of proton transfers in the reactions of 2-furyllithium and 2-thienyllithium, while the reaction of 5-methyl-2-furyllithium seems to proceed through an electron transfer as the first step. Copyright © 2003 John Wiley & Sons, Ltd.

Registro:

Documento: Artículo
Título:Reactions of lithiated aromatic heterocycles with carbon monoxide
Autor:García Liñares, G.E.; Nudelman, N.S.
Filiación:Depto. de Quím. Orgán., Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, Pab. II, P.3, 1428 Buenos Aires, Argentina
Facultad de Ciencias Exactas, UBA, Ciudad Universitaria, Pab II, P.3, 1428 Buenos Aires, Argentina
Inst. for Mat. Chem. and Engineering, Kyushu University, 6-10-1 Hakozaki, Fukuoka 812-8581, Japan
Palabras clave:Carbonylation; Electron transfer; Heterocycles; Mechanism; Organolithium; Radicals; Aromatic hydrocarbons; Carbon monoxide; Carbonylation; Derivatives; Lithium; Heterocycles; Reaction kinetics
Año:2003
Volumen:16
Número:8
Página de inicio:569
Página de fin:576
DOI: http://dx.doi.org/10.1002/poc.661
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_n8_p569_GarciaLinares

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Citas:

---------- APA ----------
García Liñares, G.E. & Nudelman, N.S. (2003) . Reactions of lithiated aromatic heterocycles with carbon monoxide. Journal of Physical Organic Chemistry, 16(8), 569-576.
http://dx.doi.org/10.1002/poc.661
---------- CHICAGO ----------
García Liñares, G.E., Nudelman, N.S. "Reactions of lithiated aromatic heterocycles with carbon monoxide" . Journal of Physical Organic Chemistry 16, no. 8 (2003) : 569-576.
http://dx.doi.org/10.1002/poc.661
---------- MLA ----------
García Liñares, G.E., Nudelman, N.S. "Reactions of lithiated aromatic heterocycles with carbon monoxide" . Journal of Physical Organic Chemistry, vol. 16, no. 8, 2003, pp. 569-576.
http://dx.doi.org/10.1002/poc.661
---------- VANCOUVER ----------
García Liñares, G.E., Nudelman, N.S. Reactions of lithiated aromatic heterocycles with carbon monoxide. J Phys Org Chem. 2003;16(8):569-576.
http://dx.doi.org/10.1002/poc.661