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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2002
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau http://hdl.handle.net/20.500.12110/paper_14246376_v2002_n5_p139_Bodineau |
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paper:paper_14246376_v2002_n5_p139_Bodineau2023-06-08T16:13:52Z 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 García, Graciela Viviana 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. 2002 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau 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 García, Graciela Viviana 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. |
| author |
García, Graciela Viviana |
| author_facet |
García, Graciela Viviana |
| author_sort |
García, Graciela Viviana |
| 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 |
| publishDate |
2002 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2002_n5_p139_Bodineau http://hdl.handle.net/20.500.12110/paper_14246376_v2002_n5_p139_Bodineau |
| work_keys_str_mv |
AT garciagracielaviviana whenaveryfastradicalprobecyclizationhintsatacarbanionicintermediateratherthanataradicaloneafurtherproofofapolarmechanismforthearylbromidealkyllithiumexchangereaction |
| _version_ |
1768544698773798912 |