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Abstract:

A new, very fast aryl radical clock, the 2-bromophenyl 3-phenyl-2-propenyl ether 1, was reacted with n-BuLi in THF. A large amount of cyclized product was formed. Such a product could have arisen from an efficient cyclization of a radical formed by dissociation of the radical anion yielded by an ET to 1. Evolution with time, temperature effects and deuteration results, strongly (hint, however, that the mechanism of this exchange reaction is rather of the polar type (SN2 or "ate complex") in agreement with previous reports from the literature based on evidences gained by other types of approaches. The carbanionic cyclization described here is one of the fastest ever reported.

Registro:

Documento: Artículo
Título:When a very fast radical probe cyclization hints at a carbanionicintermediate rather than at a radical one: A further proof of a polarmechanismfor the aryl bromide-alkyllithium exchange reaction
Autor:Bodineau, N.; Nudelman, N.S.; García, G.V.; Mattalia, J.-M.; Martins, R.; Arbelot, M.; Chanon, M.
Filiación:Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428, Buenos Aires, Argentina
Laboratoire AM3, Faculte des Sciences de Saint Jerome, case 561, 13397 Marseille Cedex 20, France
Palabras clave:2 bromophenyl 3 phenyl 2 propenyl ether; anion; bromine derivative; lithium derivative; n butyllithiuim; radical; tetrahydrofuran; unclassified drug; anion exchange; article; cyclization; dissociation; molecular evolution; radical reaction; temperature sensitivity
Año:2002
Volumen:2002
Número:5
Página de inicio:139
Página de fin:150
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:14246376
CAS:tetrahydrofuran, 109-99-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau

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Citas:

---------- APA ----------
Bodineau, N., Nudelman, N.S., García, G.V., Mattalia, J.-M., Martins, R., Arbelot, M. & Chanon, M. (2002) . When a very fast radical probe cyclization hints at a carbanionicintermediate rather than at a radical one: A further proof of a polarmechanismfor the aryl bromide-alkyllithium exchange reaction. Arkivoc, 2002(5), 139-150.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau [ ]
---------- CHICAGO ----------
Bodineau, N., Nudelman, N.S., García, G.V., Mattalia, J.-M., Martins, R., Arbelot, M., et al. "When a very fast radical probe cyclization hints at a carbanionicintermediate rather than at a radical one: A further proof of a polarmechanismfor the aryl bromide-alkyllithium exchange reaction" . Arkivoc 2002, no. 5 (2002) : 139-150.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau [ ]
---------- MLA ----------
Bodineau, N., Nudelman, N.S., García, G.V., Mattalia, J.-M., Martins, R., Arbelot, M., et al. "When a very fast radical probe cyclization hints at a carbanionicintermediate rather than at a radical one: A further proof of a polarmechanismfor the aryl bromide-alkyllithium exchange reaction" . Arkivoc, vol. 2002, no. 5, 2002, pp. 139-150.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau [ ]
---------- VANCOUVER ----------
Bodineau, N., Nudelman, N.S., García, G.V., Mattalia, J.-M., Martins, R., Arbelot, M., et al. When a very fast radical probe cyclization hints at a carbanionicintermediate rather than at a radical one: A further proof of a polarmechanismfor the aryl bromide-alkyllithium exchange reaction. Arkivoc. 2002;2002(5):139-150.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau [ ]