Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes

Detalhes bibliográficos
Autor(a) principal: Ribeiro,Rodrigo da Silva
Data de Publicação: 2012
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=S0103-50532012000200006
Resumo: Dichloroiodoisocyanuric acid was prepared in 93% by heating trichloroisocyanuric acid with 1.05 mol equiv. of iodine. This new reagent is very efficient for regioselective electrophilic iodination of activated arenes. Alkenes react with dichloroiodoisocyanuric acid in the presence of oxygenated nucleophiles (water, alcohols, and acetic acid), leading to the corresponding iodohydrins, β-iodoethers and β-iodoacetates with reaction times of less than one minute and with a high degree of regioselectivity. Enol ethers resulted in the regioselective formation of the corresponding iodine-dialkylacetals. Experimental results and DFT calculations showed that dichoroiodoisocyanuric acid is more reactive with unsaturated systems than triiodoisocyanuric acid.
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spelling Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenesalkenesareneselectrophilic additionelectrophilic aromatic substitutionhalogenationDichloroiodoisocyanuric acid was prepared in 93% by heating trichloroisocyanuric acid with 1.05 mol equiv. of iodine. This new reagent is very efficient for regioselective electrophilic iodination of activated arenes. Alkenes react with dichloroiodoisocyanuric acid in the presence of oxygenated nucleophiles (water, alcohols, and acetic acid), leading to the corresponding iodohydrins, β-iodoethers and β-iodoacetates with reaction times of less than one minute and with a high degree of regioselectivity. Enol ethers resulted in the regioselective formation of the corresponding iodine-dialkylacetals. Experimental results and DFT calculations showed that dichoroiodoisocyanuric acid is more reactive with unsaturated systems than triiodoisocyanuric acid.Sociedade Brasileira de Química2012-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000200006Journal of the Brazilian Chemical Society v.23 n.2 2012reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532012000200006info:eu-repo/semantics/openAccessRibeiro,Rodrigo da SilvaEsteves,Pierre M.Mattos,Marcio C. S. deeng2012-03-02T00:00:00Zoai:scielo:S0103-50532012000200006Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2012-03-02T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
title Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
spellingShingle Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
Ribeiro,Rodrigo da Silva
alkenes
arenes
electrophilic addition
electrophilic aromatic substitution
halogenation
title_short Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
title_full Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
title_fullStr Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
title_full_unstemmed Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
title_sort Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes
author Ribeiro,Rodrigo da Silva
author_facet Ribeiro,Rodrigo da Silva
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 Ribeiro,Rodrigo da Silva
Esteves,Pierre M.
Mattos,Marcio C. S. de
dc.subject.por.fl_str_mv alkenes
arenes
electrophilic addition
electrophilic aromatic substitution
halogenation
topic alkenes
arenes
electrophilic addition
electrophilic aromatic substitution
halogenation
description Dichloroiodoisocyanuric acid was prepared in 93% by heating trichloroisocyanuric acid with 1.05 mol equiv. of iodine. This new reagent is very efficient for regioselective electrophilic iodination of activated arenes. Alkenes react with dichloroiodoisocyanuric acid in the presence of oxygenated nucleophiles (water, alcohols, and acetic acid), leading to the corresponding iodohydrins, β-iodoethers and β-iodoacetates with reaction times of less than one minute and with a high degree of regioselectivity. Enol ethers resulted in the regioselective formation of the corresponding iodine-dialkylacetals. Experimental results and DFT calculations showed that dichoroiodoisocyanuric acid is more reactive with unsaturated systems than triiodoisocyanuric acid.
publishDate 2012
dc.date.none.fl_str_mv 2012-02-01
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=S0103-50532012000200006
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000200006
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532012000200006
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.23 n.2 2012
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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