A green Hunsdiecker reaction of cinnamic acids

Detalhes bibliográficos
Autor(a) principal: Sodré,Leonardo R.
Data de Publicação: 2013
Outros Autores: Esteves,Pierre M., Mattos,Marcio C. S. de
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=S0103-50532013000200006
Resumo: Tribromo- and trichloroisocyanuric acids react with cinnamic acids in NaOH/H2O/Et2O at room temperature to produce (E)-2-halostyrenes regioselectively in 25-95% yield. Mechanism studies using Hammett correlations and DFT (density functional theory) calculations have shown that this reaction has as rate determining step the electrophilic addition of chlorine atom to the double bond.
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spelling A green Hunsdiecker reaction of cinnamic acidsstyrenecinnamic acidHunsdiecker reactiontrihaloisocyanuric acidDFTTribromo- and trichloroisocyanuric acids react with cinnamic acids in NaOH/H2O/Et2O at room temperature to produce (E)-2-halostyrenes regioselectively in 25-95% yield. Mechanism studies using Hammett correlations and DFT (density functional theory) calculations have shown that this reaction has as rate determining step the electrophilic addition of chlorine atom to the double bond.Sociedade Brasileira de Química2013-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000200006Journal of the Brazilian Chemical Society v.24 n.2 2013reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130027info:eu-repo/semantics/openAccessSodré,Leonardo R.Esteves,Pierre M.Mattos,Marcio C. S. deeng2013-05-20T00:00:00Zoai:scielo:S0103-50532013000200006Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2013-05-20T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A green Hunsdiecker reaction of cinnamic acids
title A green Hunsdiecker reaction of cinnamic acids
spellingShingle A green Hunsdiecker reaction of cinnamic acids
Sodré,Leonardo R.
styrene
cinnamic acid
Hunsdiecker reaction
trihaloisocyanuric acid
DFT
title_short A green Hunsdiecker reaction of cinnamic acids
title_full A green Hunsdiecker reaction of cinnamic acids
title_fullStr A green Hunsdiecker reaction of cinnamic acids
title_full_unstemmed A green Hunsdiecker reaction of cinnamic acids
title_sort A green Hunsdiecker reaction of cinnamic acids
author Sodré,Leonardo R.
author_facet Sodré,Leonardo R.
Esteves,Pierre M.
Mattos,Marcio C. S. de
author_role author
author2 Esteves,Pierre M.
Mattos,Marcio C. S. de
author2_role author
author
dc.contributor.author.fl_str_mv Sodré,Leonardo R.
Esteves,Pierre M.
Mattos,Marcio C. S. de
dc.subject.por.fl_str_mv styrene
cinnamic acid
Hunsdiecker reaction
trihaloisocyanuric acid
DFT
topic styrene
cinnamic acid
Hunsdiecker reaction
trihaloisocyanuric acid
DFT
description Tribromo- and trichloroisocyanuric acids react with cinnamic acids in NaOH/H2O/Et2O at room temperature to produce (E)-2-halostyrenes regioselectively in 25-95% yield. Mechanism studies using Hammett correlations and DFT (density functional theory) calculations have shown that this reaction has as rate determining step the electrophilic addition of chlorine atom to the double bond.
publishDate 2013
dc.date.none.fl_str_mv 2013-02-01
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=S0103-50532013000200006
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000200006
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20130027
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.24 n.2 2013
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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