Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions

Detalhes bibliográficos
Autor(a) principal: Lenardão,Eder J.
Data de Publicação: 2009
Outros Autores: Trecha,Danusia O., Ferreira,Patrícia da C., Jacob,Raquel G., Perin,Gelson
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000100016
Resumo: A general, clean and easy method for the conjugated addition of thiols to citral promoted by KF/Al2O3 under solvent-free or using glycerin as recyclable solvent at room temperature is described. It was found that the solvent-free protocol is applicable to the direct reaction of thiophenol with the essential oil of lemon grass (Cymbopogon citratus) to afford directly 3,7-dimethyl-3-(phenylthio)oct-6-enal, a potential bactericide agent. The method was extended to other electron-poor alkenes with excellent results. For the solvent-free protocol, the use of microwave irradiation facilitated the procedure and accelerates the reaction. The catalytic system and glycerin can be reused up to three times without previous treatment with comparable activity.
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spelling Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditionssolvent-free1,4-addition of thiolsglycerincitral and citronellalgreen chemistryA general, clean and easy method for the conjugated addition of thiols to citral promoted by KF/Al2O3 under solvent-free or using glycerin as recyclable solvent at room temperature is described. It was found that the solvent-free protocol is applicable to the direct reaction of thiophenol with the essential oil of lemon grass (Cymbopogon citratus) to afford directly 3,7-dimethyl-3-(phenylthio)oct-6-enal, a potential bactericide agent. The method was extended to other electron-poor alkenes with excellent results. For the solvent-free protocol, the use of microwave irradiation facilitated the procedure and accelerates the reaction. The catalytic system and glycerin can be reused up to three times without previous treatment with comparable activity.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000100016Journal of the Brazilian Chemical Society v.20 n.1 2009reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532009000100016info:eu-repo/semantics/openAccessLenardão,Eder J.Trecha,Danusia O.Ferreira,Patrícia da C.Jacob,Raquel G.Perin,Gelsoneng2009-01-14T00:00:00Zoai:scielo:S0103-50532009000100016Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2009-01-14T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
title Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
spellingShingle Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
Lenardão,Eder J.
solvent-free
1,4-addition of thiols
glycerin
citral and citronellal
green chemistry
title_short Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
title_full Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
title_fullStr Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
title_full_unstemmed Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
title_sort Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions
author Lenardão,Eder J.
author_facet Lenardão,Eder J.
Trecha,Danusia O.
Ferreira,Patrícia da C.
Jacob,Raquel G.
Perin,Gelson
author_role author
author2 Trecha,Danusia O.
Ferreira,Patrícia da C.
Jacob,Raquel G.
Perin,Gelson
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Lenardão,Eder J.
Trecha,Danusia O.
Ferreira,Patrícia da C.
Jacob,Raquel G.
Perin,Gelson
dc.subject.por.fl_str_mv solvent-free
1,4-addition of thiols
glycerin
citral and citronellal
green chemistry
topic solvent-free
1,4-addition of thiols
glycerin
citral and citronellal
green chemistry
description A general, clean and easy method for the conjugated addition of thiols to citral promoted by KF/Al2O3 under solvent-free or using glycerin as recyclable solvent at room temperature is described. It was found that the solvent-free protocol is applicable to the direct reaction of thiophenol with the essential oil of lemon grass (Cymbopogon citratus) to afford directly 3,7-dimethyl-3-(phenylthio)oct-6-enal, a potential bactericide agent. The method was extended to other electron-poor alkenes with excellent results. For the solvent-free protocol, the use of microwave irradiation facilitated the procedure and accelerates the reaction. The catalytic system and glycerin can be reused up to three times without previous treatment with comparable activity.
publishDate 2009
dc.date.none.fl_str_mv 2009-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000100016
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000100016
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532009000100016
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
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 Journal of the Brazilian Chemical Society v.20 n.1 2009
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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