Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
Autor(a) principal: | |
---|---|
Data de Publicação: | 2016 |
Outros Autores: | , , , |
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. |
id |
SBQ-2_f9088102a4d2b45dd054cddb6ad702a0 |
---|---|
oai_identifier_str |
oai:scielo:S0103-50532016001102046 |
network_acronym_str |
SBQ-2 |
network_name_str |
Journal of the Brazilian Chemical Society (Online) |
repository_id_str |
|
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 |
_version_ |
1750318178792112128 |