The reaction of (R)-limonene with S-thioacids

Detalhes bibliográficos
Autor(a) principal: Mattos,Marcio C. S. de
Data de Publicação: 2007
Outros Autores: Bernini,Rafael Berrelho
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=S0103-50532007000500029
Resumo: The reaction of (R)-limonene with equimolar amount of S-thioacetic or S-thiobenzoic acids in refluxing toluene proceeded regioselectively in anti-Markovnikoff fashion forming 9-[(4R, 8RS)-p-menthenyl] S-thiocarboxylates (71 and 61% yield, respectively). The montmorillonite K-10 clay-catalyzed reaction of (R)-limonene with S-thioacetic acid led to the S-thioester (65%) along with p-menthadienes and p-cymene. It was observed that K-10 clay promoted the isomerization of limonene to p-menthadienes and further disproportionation to p-cymene.
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spelling The reaction of (R)-limonene with S-thioacids(R)-limoneneS-thioestermontmorillonite K-10The reaction of (R)-limonene with equimolar amount of S-thioacetic or S-thiobenzoic acids in refluxing toluene proceeded regioselectively in anti-Markovnikoff fashion forming 9-[(4R, 8RS)-p-menthenyl] S-thiocarboxylates (71 and 61% yield, respectively). The montmorillonite K-10 clay-catalyzed reaction of (R)-limonene with S-thioacetic acid led to the S-thioester (65%) along with p-menthadienes and p-cymene. It was observed that K-10 clay promoted the isomerization of limonene to p-menthadienes and further disproportionation to p-cymene.Sociedade Brasileira de Química2007-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000500029Journal of the Brazilian Chemical Society v.18 n.5 2007reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532007000500029info:eu-repo/semantics/openAccessMattos,Marcio C. S. deBernini,Rafael Berrelhoeng2007-10-29T00:00:00Zoai:scielo:S0103-50532007000500029Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2007-10-29T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv The reaction of (R)-limonene with S-thioacids
title The reaction of (R)-limonene with S-thioacids
spellingShingle The reaction of (R)-limonene with S-thioacids
Mattos,Marcio C. S. de
(R)-limonene
S-thioester
montmorillonite K-10
title_short The reaction of (R)-limonene with S-thioacids
title_full The reaction of (R)-limonene with S-thioacids
title_fullStr The reaction of (R)-limonene with S-thioacids
title_full_unstemmed The reaction of (R)-limonene with S-thioacids
title_sort The reaction of (R)-limonene with S-thioacids
author Mattos,Marcio C. S. de
author_facet Mattos,Marcio C. S. de
Bernini,Rafael Berrelho
author_role author
author2 Bernini,Rafael Berrelho
author2_role author
dc.contributor.author.fl_str_mv Mattos,Marcio C. S. de
Bernini,Rafael Berrelho
dc.subject.por.fl_str_mv (R)-limonene
S-thioester
montmorillonite K-10
topic (R)-limonene
S-thioester
montmorillonite K-10
description The reaction of (R)-limonene with equimolar amount of S-thioacetic or S-thiobenzoic acids in refluxing toluene proceeded regioselectively in anti-Markovnikoff fashion forming 9-[(4R, 8RS)-p-menthenyl] S-thiocarboxylates (71 and 61% yield, respectively). The montmorillonite K-10 clay-catalyzed reaction of (R)-limonene with S-thioacetic acid led to the S-thioester (65%) along with p-menthadienes and p-cymene. It was observed that K-10 clay promoted the isomerization of limonene to p-menthadienes and further disproportionation to p-cymene.
publishDate 2007
dc.date.none.fl_str_mv 2007-01-01
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=S0103-50532007000500029
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000500029
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532007000500029
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.18 n.5 2007
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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