Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/14460 |
Resumo: | In the present study, a series of aryl alkynols functionalized was subjected to intramolecular cyclization reaction promoted by iron(III) chloride and diorganyl dichalcogenides allowing the synthesis of 2-organoselenyl-naphthalenes. The mutual action between the diorganyl dichalcogenide and iron (III) chloride, in a 0.6: 0.75 mole ratio, was essential for the achievement of the products in good yields. The cyclization reaction tolerated a variety of functional groups, such as electron-donating group, electron-withdrawing groups and bulky groups. It was obtained the naphthalene derivatives exclusively via 6-endo-dig cyclization, giving thirty new compounds in 45-90% yields. In addition, using these compounds it was possible to carry out a selenium-lithium exchange reaction, giving the lithium intermediate derivatives, which were captured by electrophiles, leading to five new compounds in 45-96% yields. |
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spelling |
2018-10-04T19:57:52Z2018-10-04T19:57:52Z2017-07-31http://repositorio.ufsm.br/handle/1/14460In the present study, a series of aryl alkynols functionalized was subjected to intramolecular cyclization reaction promoted by iron(III) chloride and diorganyl dichalcogenides allowing the synthesis of 2-organoselenyl-naphthalenes. The mutual action between the diorganyl dichalcogenide and iron (III) chloride, in a 0.6: 0.75 mole ratio, was essential for the achievement of the products in good yields. The cyclization reaction tolerated a variety of functional groups, such as electron-donating group, electron-withdrawing groups and bulky groups. It was obtained the naphthalene derivatives exclusively via 6-endo-dig cyclization, giving thirty new compounds in 45-90% yields. In addition, using these compounds it was possible to carry out a selenium-lithium exchange reaction, giving the lithium intermediate derivatives, which were captured by electrophiles, leading to five new compounds in 45-96% yields.No presente trabalho, uma série de aril alquinois funcionalizados foi submetida à reação de ciclização intramolecular promovida por FeCl3 com dicalcogenetos de diorganoíla, possibilitando a síntese de 2-organoselenil-naftalenos. A ação mútua entre o dicalcogeneto de diorganoíla e o cloreto de ferro (III), em proporções molares de 0,6: 0,75, foi essencial para a obtenção dos produtos em bons rendimentos. Destaca-se a tolerância da reação a uma variedade de grupos funcionais, tais como grupos doadores e retiradores de elétrons, bem como grupos volumosos. Os derivados de naftalenos foram obtidos exclusivamente por meio de um processo de ciclização 6-endo-dig, resultando na formação de trinta novos exemplos com rendimentos que variaram de 45-90%. Com o desenvolvimento desta metodologia também foi possível realizar uma troca selênio-lítio, formando um intermediário de lítio, seguida da captura de um eletrófilo, levando a obtenção de cinco novos compostos em uma faixa de rendimento de 45-96%.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessCiclização intramolecularDicalcogenetos de diorganoílaAlquinoisIntramolecular cyclizationDiorganyl dichalcogenidesAlkynolsCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAFormação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenosSequential carbon-carbon/carbon-seleniun bonds formation mediated by iron(iii) chloride and diorganyl diselenides: synthesis and reactivity of 2-organochalcogenil-naphthalenesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Godoi, Benhur dehttp://lattes.cnpq.br/7951653430970975Schumacher, Ricardo Fredericohttp://lattes.cnpq.br/7856034546434135http://lattes.cnpq.br/0302295391496951Recchi, Ana Maria Spohr100600000000600b21a898a-0ab0-4f33-b980-2b55ef590b94435a47a4-e0a4-474a-84ee-b5fbc324508473af17fe-4603-4a92-9890-9ab29a107d4e6a26f817-0d52-41d8-9183-c785c92d110areponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos |
dc.title.alternative.eng.fl_str_mv |
Sequential carbon-carbon/carbon-seleniun bonds formation mediated by iron(iii) chloride and diorganyl diselenides: synthesis and reactivity of 2-organochalcogenil-naphthalenes |
title |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos |
spellingShingle |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos Recchi, Ana Maria Spohr Ciclização intramolecular Dicalcogenetos de diorganoíla Alquinois Intramolecular cyclization Diorganyl dichalcogenides Alkynols CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos |
title_full |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos |
title_fullStr |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos |
title_full_unstemmed |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos |
title_sort |
Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos |
author |
Recchi, Ana Maria Spohr |
author_facet |
Recchi, Ana Maria Spohr |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zeni, Gilson Rogério |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/2355575631197937 |
dc.contributor.referee1.fl_str_mv |
Godoi, Benhur de |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/7951653430970975 |
dc.contributor.referee2.fl_str_mv |
Schumacher, Ricardo Frederico |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/7856034546434135 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0302295391496951 |
dc.contributor.author.fl_str_mv |
Recchi, Ana Maria Spohr |
contributor_str_mv |
Zeni, Gilson Rogério Godoi, Benhur de Schumacher, Ricardo Frederico |
dc.subject.por.fl_str_mv |
Ciclização intramolecular Dicalcogenetos de diorganoíla Alquinois |
topic |
Ciclização intramolecular Dicalcogenetos de diorganoíla Alquinois Intramolecular cyclization Diorganyl dichalcogenides Alkynols CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Intramolecular cyclization Diorganyl dichalcogenides Alkynols |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In the present study, a series of aryl alkynols functionalized was subjected to intramolecular cyclization reaction promoted by iron(III) chloride and diorganyl dichalcogenides allowing the synthesis of 2-organoselenyl-naphthalenes. The mutual action between the diorganyl dichalcogenide and iron (III) chloride, in a 0.6: 0.75 mole ratio, was essential for the achievement of the products in good yields. The cyclization reaction tolerated a variety of functional groups, such as electron-donating group, electron-withdrawing groups and bulky groups. It was obtained the naphthalene derivatives exclusively via 6-endo-dig cyclization, giving thirty new compounds in 45-90% yields. In addition, using these compounds it was possible to carry out a selenium-lithium exchange reaction, giving the lithium intermediate derivatives, which were captured by electrophiles, leading to five new compounds in 45-96% yields. |
publishDate |
2017 |
dc.date.issued.fl_str_mv |
2017-07-31 |
dc.date.accessioned.fl_str_mv |
2018-10-04T19:57:52Z |
dc.date.available.fl_str_mv |
2018-10-04T19:57:52Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/14460 |
url |
http://repositorio.ufsm.br/handle/1/14460 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
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Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
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Universidade Federal de Santa Maria (UFSM) |
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UFSM |
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Manancial - Repositório Digital da UFSM |
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Manancial - Repositório Digital da UFSM |
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