Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos

Detalhes bibliográficos
Ano de defesa: 2007
Autor(a) principal: Schneid, Caroline Cassalha Schneider lattes
Orientador(a): Zeni, Gilson Rogério lattes
Banca de defesa: Santos, Alcindo Aparecido dos, Perin, Gelson
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: Brasil
Palavras-chave em Português:
Síntese estereosseletiva
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/23851
Resumo: In the work presented herein we describe the reaction of diorganoyl dichalcogenides with terminal alkynes under catalyst free conditions, by one pot procedure, to prepare unsymmetrical bis- and tris-chalcogenide alkenes selectively, avoiding the previous preparation of chalcogenealkynes. The reaction proceeded cleanly under mild reaction conditions and the addition of dichalcogenides to alkynes occurred stereoselectively to give exclusively the corresponding Z isomers. The selectivity control of reaction was governed by the effective participation of the hydroxyl group from propargyl alcohols. Indeed, unsymmetrical bis-chalcogenide alkenes were obtained with propargyl alcohol having the acidic hydroxyl group hydrogen. On the other hand, unsymmetrical tris-chalcogenide alkenes were exclusively obtained from alkynes with no potentially acidic hydroxyl group hydrogen.
id UFSM_80bfc6c6a489ea79181d916b26aada3d
oai_identifier_str oai:repositorio.ufsm.br:1/23851
network_acronym_str UFSM
network_name_str Biblioteca Digital de Teses e Dissertações do UFSM
repository_id_str
spelling 2022-03-23T13:22:47Z2022-03-23T13:22:47Z2007-02-27http://repositorio.ufsm.br/handle/1/23851In the work presented herein we describe the reaction of diorganoyl dichalcogenides with terminal alkynes under catalyst free conditions, by one pot procedure, to prepare unsymmetrical bis- and tris-chalcogenide alkenes selectively, avoiding the previous preparation of chalcogenealkynes. The reaction proceeded cleanly under mild reaction conditions and the addition of dichalcogenides to alkynes occurred stereoselectively to give exclusively the corresponding Z isomers. The selectivity control of reaction was governed by the effective participation of the hydroxyl group from propargyl alcohols. Indeed, unsymmetrical bis-chalcogenide alkenes were obtained with propargyl alcohol having the acidic hydroxyl group hydrogen. On the other hand, unsymmetrical tris-chalcogenide alkenes were exclusively obtained from alkynes with no potentially acidic hydroxyl group hydrogen.No presente trabalho desenvolveu-se a reação de dicalcogenetos de diorganoila mistos com alquinos terminais, na ausência de catalisador, para a preparação seletiva de bis- e tris-calcogenetos vinílicos mistos, através de um procedimento “one-pot”, evitando a preparação prévia de calcogenoacetilenos. A reação ocorreu facilmente sob condições reacionais brandas e a adição dos dicalcogenetos de diorganoila mistos a acetilenos ocorreu de maneira estereosseletiva fornecendo exclusivamente o isômero Z. O controle estereosseletivo foi governado pela participação efetiva do grupamento hidroxila, proveniente dos álcoois propargílicos. Efetivamente, os bis-calcogenetos vinílicos mistos foram obtidos a partir de álcoois propargílicos, que possuem grupamento hidroxila com hidrogênio ácido. Por outro lado, os tris-calcogenetos vinílicos mistos foram obtidos exclusivamente a partir de acetilenos não hidroxilados.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSporUniversidade 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/openAccessSíntese estereosseletivaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistosStereoselective synthesis of unsymmetrical bis- and tris-chalcogenide alkenesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZeni, Gilson Rogério400170d5-13d8-4075-bc58-ecabc75bc542600Zeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937http://lattes.cnpq.br/2355575631197937Santos, Alcindo Aparecido dosPerin, Gelsonhttp://lattes.cnpq.br/2305432767739828Schneid, Caroline Cassalha Schneider100600000000600600600600600b21a898a-0ab0-4f33-b980-2b55ef590b94744f511e-d154-4bc0-9504-ee0fa20bbc681c2375a4-1870-4869-b020-c586f03d0b821fdc0f55-b165-4805-8083-0d6d98ff1a25reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2007_SCHNEIDER_CAROLINE.pdfDIS_PPGQUIMICA_2007_SCHNEIDER_CAROLINE.pdfDissertaçãoapplication/pdf440853http://repositorio.ufsm.br/bitstream/1/23851/1/DIS_PPGQUIMICA_2007_SCHNEIDER_CAROLINE.pdf7b415d5acbc959d999e1c8528375a751MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/23851/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/23851/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/238512022-03-23 10:22:47.479oai:repositorio.ufsm.br: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 Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-03-23T13:22:47Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
dc.title.alternative.eng.fl_str_mv Stereoselective synthesis of unsymmetrical bis- and tris-chalcogenide alkenes
title Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
spellingShingle Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
Schneid, Caroline Cassalha Schneider
Síntese estereosseletiva
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
title_full Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
title_fullStr Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
title_full_unstemmed Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
title_sort Síntese estereosseletiva de bis- e tris-calcogenetos vinílicos mistos
author Schneid, Caroline Cassalha Schneider
author_facet Schneid, Caroline Cassalha Schneider
author_role author
dc.contributor.advisor1.fl_str_mv Zeni, Gilson Rogério
dc.contributor.advisor2.fl_str_mv Zeni, Gilson Rogério
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/2355575631197937
dc.contributor.advisor2Lattes.fl_str_mv http://lattes.cnpq.br/2355575631197937
dc.contributor.referee1.fl_str_mv Santos, Alcindo Aparecido dos
dc.contributor.referee2.fl_str_mv Perin, Gelson
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/2305432767739828
dc.contributor.author.fl_str_mv Schneid, Caroline Cassalha Schneider
contributor_str_mv Zeni, Gilson Rogério
Zeni, Gilson Rogério
Santos, Alcindo Aparecido dos
Perin, Gelson
dc.subject.por.fl_str_mv Síntese estereosseletiva
topic Síntese estereosseletiva
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In the work presented herein we describe the reaction of diorganoyl dichalcogenides with terminal alkynes under catalyst free conditions, by one pot procedure, to prepare unsymmetrical bis- and tris-chalcogenide alkenes selectively, avoiding the previous preparation of chalcogenealkynes. The reaction proceeded cleanly under mild reaction conditions and the addition of dichalcogenides to alkynes occurred stereoselectively to give exclusively the corresponding Z isomers. The selectivity control of reaction was governed by the effective participation of the hydroxyl group from propargyl alcohols. Indeed, unsymmetrical bis-chalcogenide alkenes were obtained with propargyl alcohol having the acidic hydroxyl group hydrogen. On the other hand, unsymmetrical tris-chalcogenide alkenes were exclusively obtained from alkynes with no potentially acidic hydroxyl group hydrogen.
publishDate 2007
dc.date.issued.fl_str_mv 2007-02-27
dc.date.accessioned.fl_str_mv 2022-03-23T13:22:47Z
dc.date.available.fl_str_mv 2022-03-23T13:22:47Z
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/1/23851
url http://repositorio.ufsm.br/handle/1/23851
dc.language.iso.fl_str_mv por
language por
dc.relation.cnpq.fl_str_mv 100600000000
dc.relation.confidence.fl_str_mv 600
600
600
600
600
dc.relation.authority.fl_str_mv b21a898a-0ab0-4f33-b980-2b55ef590b94
744f511e-d154-4bc0-9504-ee0fa20bbc68
1c2375a4-1870-4869-b020-c586f03d0b82
1fdc0f55-b165-4805-8083-0d6d98ff1a25
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
rights_invalid_str_mv 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:Biblioteca Digital de Teses e Dissertações do UFSM
instname:Universidade Federal de Santa Maria (UFSM)
instacron:UFSM
instname_str Universidade Federal de Santa Maria (UFSM)
instacron_str UFSM
institution UFSM
reponame_str Biblioteca Digital de Teses e Dissertações do UFSM
collection Biblioteca Digital de Teses e Dissertações do UFSM
bitstream.url.fl_str_mv http://repositorio.ufsm.br/bitstream/1/23851/1/DIS_PPGQUIMICA_2007_SCHNEIDER_CAROLINE.pdf
http://repositorio.ufsm.br/bitstream/1/23851/2/license_rdf
http://repositorio.ufsm.br/bitstream/1/23851/3/license.txt
bitstream.checksum.fl_str_mv 7b415d5acbc959d999e1c8528375a751
4460e5956bc1d1639be9ae6146a50347
2f0571ecee68693bd5cd3f17c1e075df
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
repository.name.fl_str_mv Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)
repository.mail.fl_str_mv atendimento.sib@ufsm.br||tedebc@gmail.com
_version_ 1793240145639505920

Registros relacionados