Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3

Detalhes bibliográficos
Autor(a) principal: Andrade, Carlos Kleber Z.
Data de Publicação: 2004
Outros Autores: Vercillo, Otilie E., Rodrigues, Juliana P., Silveira, Denise P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UnB
Texto Completo: http://repositorio.unb.br/handle/10482/26245
https://dx.doi.org/10.1590/S0103-50532004000600005
Resumo: Niobium pentachloride, tantalum pentachloride and indium trichloride efficiently catalysed the cyclization of (R)-citronellal to a mixture of isopulegol and neoisopulegol in good yields. A comparative study was carried out which demonstrated that NbCl5 is the most active Lewis acid whereas InCl3 is the most selective one. The selectivity of the reactions varied according to the Lewis acid used and to the solvent. The ene reaction of a 1,7-diene was also investigated. In this case, all Lewis acids tested showed excellent selectivity.
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spelling Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3CitronelalIsopulegolReações Eno intramolecularesÁcidos de LewisSeletividadeNiobium pentachloride, tantalum pentachloride and indium trichloride efficiently catalysed the cyclization of (R)-citronellal to a mixture of isopulegol and neoisopulegol in good yields. A comparative study was carried out which demonstrated that NbCl5 is the most active Lewis acid whereas InCl3 is the most selective one. The selectivity of the reactions varied according to the Lewis acid used and to the solvent. The ene reaction of a 1,7-diene was also investigated. In this case, all Lewis acids tested showed excellent selectivity.Pentacloreto de nióbio, pentacloreto de tântalo e tricloreto de índio catalisaram eficientemente a ciclização do (R)-citronelal a uma mistura de isopulegol e neoisopulegol, em bons rendimentos. Um estudo comparativo foi realizado demonstrando que NbCl5 é o ácido de Lewis mais ativo enquanto que InCl3 é o mais seletivo. A seletividade das reações variou de acordo com o ácido de Lewis utilizado e o solvente. NbCl5 e TaCl5 mostraram ausência de seletividade enquanto que o InCl3 apresentou seletividade moderada em favor do isopulegol. A reação ene de um 1,7-dieno também foi investigada. Neste caso, todos os ácidos de Lewis testados apresentaram excelente seletividade.Em processamentoSociedade Brasileira de Química2017-12-07T04:39:31Z2017-12-07T04:39:31Z2004info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfJ. Braz. Chem. Soc.,v.15,n.6,p.813-817,2004http://repositorio.unb.br/handle/10482/26245https://dx.doi.org/10.1590/S0103-50532004000600005Andrade, Carlos Kleber Z.Vercillo, Otilie E.Rodrigues, Juliana P.Silveira, Denise P.info:eu-repo/semantics/openAccessengreponame:Repositório Institucional da UnBinstname:Universidade de Brasília (UnB)instacron:UNB2024-08-28T19:04:09Zoai:repositorio.unb.br:10482/26245Repositório InstitucionalPUBhttps://repositorio.unb.br/oai/requestrepositorio@unb.bropendoar:2024-08-28T19:04:09Repositório Institucional da UnB - Universidade de Brasília (UnB)false
dc.title.none.fl_str_mv Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
title Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
spellingShingle Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
Andrade, Carlos Kleber Z.
Citronelal
Isopulegol
Reações Eno intramoleculares
Ácidos de Lewis
Seletividade
title_short Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
title_full Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
title_fullStr Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
title_full_unstemmed Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
title_sort Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3
author Andrade, Carlos Kleber Z.
author_facet Andrade, Carlos Kleber Z.
Vercillo, Otilie E.
Rodrigues, Juliana P.
Silveira, Denise P.
author_role author
author2 Vercillo, Otilie E.
Rodrigues, Juliana P.
Silveira, Denise P.
author2_role author
author
author
dc.contributor.author.fl_str_mv Andrade, Carlos Kleber Z.
Vercillo, Otilie E.
Rodrigues, Juliana P.
Silveira, Denise P.
dc.subject.por.fl_str_mv Citronelal
Isopulegol
Reações Eno intramoleculares
Ácidos de Lewis
Seletividade
topic Citronelal
Isopulegol
Reações Eno intramoleculares
Ácidos de Lewis
Seletividade
description Niobium pentachloride, tantalum pentachloride and indium trichloride efficiently catalysed the cyclization of (R)-citronellal to a mixture of isopulegol and neoisopulegol in good yields. A comparative study was carried out which demonstrated that NbCl5 is the most active Lewis acid whereas InCl3 is the most selective one. The selectivity of the reactions varied according to the Lewis acid used and to the solvent. The ene reaction of a 1,7-diene was also investigated. In this case, all Lewis acids tested showed excellent selectivity.
publishDate 2004
dc.date.none.fl_str_mv 2004
2017-12-07T04:39:31Z
2017-12-07T04:39:31Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv J. Braz. Chem. Soc.,v.15,n.6,p.813-817,2004
http://repositorio.unb.br/handle/10482/26245
https://dx.doi.org/10.1590/S0103-50532004000600005
identifier_str_mv J. Braz. Chem. Soc.,v.15,n.6,p.813-817,2004
url http://repositorio.unb.br/handle/10482/26245
https://dx.doi.org/10.1590/S0103-50532004000600005
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da UnB
instname:Universidade de Brasília (UnB)
instacron:UNB
instname_str Universidade de Brasília (UnB)
instacron_str UNB
institution UNB
reponame_str Repositório Institucional da UnB
collection Repositório Institucional da UnB
repository.name.fl_str_mv Repositório Institucional da UnB - Universidade de Brasília (UnB)
repository.mail.fl_str_mv repositorio@unb.br
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