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
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...
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| Formato: | JOUR |
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14246376_v2002_n5_p139_Bodineau |
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todo:paper_14246376_v2002_n5_p139_Bodineau2023-10-03T16:13:36Z 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 Bodineau, N. Nudelman, N.S. García, G.V. Mattalia, J.-M. Martins, R. Arbelot, M. Chanon, M. 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 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. Fil:García, G.V. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14246376_v2002_n5_p139_Bodineau |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Bodineau, N. Nudelman, N.S. García, G.V. Mattalia, J.-M. Martins, R. Arbelot, M. Chanon, M. 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 |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Bodineau, N. Nudelman, N.S. García, G.V. Mattalia, J.-M. Martins, R. Arbelot, M. Chanon, M. |
| author_facet |
Bodineau, N. Nudelman, N.S. García, G.V. Mattalia, J.-M. Martins, R. Arbelot, M. Chanon, M. |
| author_sort |
Bodineau, N. |
| title |
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 |
| title_short |
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 |
| title_full |
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 |
| title_fullStr |
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 |
| title_full_unstemmed |
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 |
| title_sort |
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 |
| url |
http://hdl.handle.net/20.500.12110/paper_14246376_v2002_n5_p139_Bodineau |
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