Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400

Detalhes bibliográficos
Autor(a) principal: Lara,Renata G.
Data de Publicação: 2016
Outros Autores: Soares,Liane K., Jacob,Raquel G., Schumacher,Ricardo F., 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=S0103-50532016001102046
Resumo: We present here our results on the temperature controlled, selective hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes with nucleophilic species of selenium, tellurium and sulfur generated in situ from the respective diaryl dichalcogenide and NaBH4. Using polyethylene glycol (PEG)-400 at 30 ºC the (Z)-chalcogenoenynes are obtained and at 90 ºC the (Z,Z)-bis-chalcogen-1,3-butadienes are produced in good to excellent yields. Alternatively to conventional oil bath heating, the use of microwave irradiation is also presented as an alternative energy source that provides the expected products in few minutes.
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spelling Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400organochalcogensPEG-400enynemicrowave irradiation1,3-butadienesWe present here our results on the temperature controlled, selective hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes with nucleophilic species of selenium, tellurium and sulfur generated in situ from the respective diaryl dichalcogenide and NaBH4. Using polyethylene glycol (PEG)-400 at 30 ºC the (Z)-chalcogenoenynes are obtained and at 90 ºC the (Z,Z)-bis-chalcogen-1,3-butadienes are produced in good to excellent yields. Alternatively to conventional oil bath heating, the use of microwave irradiation is also presented as an alternative energy source that provides the expected products in few minutes.Sociedade Brasileira de Química2016-11-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001102046Journal of the Brazilian Chemical Society v.27 n.11 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160094info:eu-repo/semantics/openAccessLara,Renata G.Soares,Liane K.Jacob,Raquel G.Schumacher,Ricardo F.Perin,Gelsoneng2016-11-04T00:00:00Zoai:scielo:S0103-50532016001102046Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-11-04T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
title Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
spellingShingle Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
Lara,Renata G.
organochalcogens
PEG-400
enyne
microwave irradiation
1,3-butadienes
title_short Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
title_full Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
title_fullStr Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
title_full_unstemmed Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
title_sort Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
author Lara,Renata G.
author_facet Lara,Renata G.
Soares,Liane K.
Jacob,Raquel G.
Schumacher,Ricardo F.
Perin,Gelson
author_role author
author2 Soares,Liane K.
Jacob,Raquel G.
Schumacher,Ricardo F.
Perin,Gelson
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Lara,Renata G.
Soares,Liane K.
Jacob,Raquel G.
Schumacher,Ricardo F.
Perin,Gelson
dc.subject.por.fl_str_mv organochalcogens
PEG-400
enyne
microwave irradiation
1,3-butadienes
topic organochalcogens
PEG-400
enyne
microwave irradiation
1,3-butadienes
description We present here our results on the temperature controlled, selective hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes with nucleophilic species of selenium, tellurium and sulfur generated in situ from the respective diaryl dichalcogenide and NaBH4. Using polyethylene glycol (PEG)-400 at 30 ºC the (Z)-chalcogenoenynes are obtained and at 90 ºC the (Z,Z)-bis-chalcogen-1,3-butadienes are produced in good to excellent yields. Alternatively to conventional oil bath heating, the use of microwave irradiation is also presented as an alternative energy source that provides the expected products in few minutes.
publishDate 2016
dc.date.none.fl_str_mv 2016-11-01
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=S0103-50532016001102046
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001102046
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20160094
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.27 n.11 2016
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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