Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre

Detalhes bibliográficos
Ano de defesa: 2020
Autor(a) principal: Kazmierczak, Jean Carlo lattes
Orientador(a): Schumacher, Ricardo Frederico lattes
Banca de defesa: Rodrigues, Oscar Endrigo Dorneles, Sperança, Adriane
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:
Sais de Bunte
α-organiltio carbonílicos
β-cetoésteres
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/23519
Resumo: In this work, a series of α-organylthio carbonyl compounds were synthesizes from β-ketoesteres and Bunte salts, using NaOH as a reaction promoter in toluene at 100 ºC. The selectivity for the formation of two products, α-organylthio ketones and α-organylthio esters, is highlighted, based on the amount of base used. It was observed that when using 2 equivalents of base the formation of α-organylthio ketones is favored and when used 4 equivalents of base products α-organylthio esters are formed preferentially. Thus, it was possible to synthesize sixteen α-organylthio esters with yelds of 20 to 90% and six examples of α-organylthio ketones with yelds of 45 to 84%. Finally, the tolerance of reactions to a variety of groups with electron donating and withdrawing characteristics such as methoxy, methyl, trifluoromethane, nitro and chloro in ortho, meta and para positions is highlighted.
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spelling 2022-01-12T14:22:39Z2022-01-12T14:22:39Z2020-02-21http://repositorio.ufsm.br/handle/1/23519In this work, a series of α-organylthio carbonyl compounds were synthesizes from β-ketoesteres and Bunte salts, using NaOH as a reaction promoter in toluene at 100 ºC. The selectivity for the formation of two products, α-organylthio ketones and α-organylthio esters, is highlighted, based on the amount of base used. It was observed that when using 2 equivalents of base the formation of α-organylthio ketones is favored and when used 4 equivalents of base products α-organylthio esters are formed preferentially. Thus, it was possible to synthesize sixteen α-organylthio esters with yelds of 20 to 90% and six examples of α-organylthio ketones with yelds of 45 to 84%. Finally, the tolerance of reactions to a variety of groups with electron donating and withdrawing characteristics such as methoxy, methyl, trifluoromethane, nitro and chloro in ortho, meta and para positions is highlighted.Neste trabalho uma série de compostos α-organiltio carbonílicos foram sintetizados a partir de β-cetoésteres e sais de Bunte, utilizando NaOH como promotor da reação em tolueno a 100 °C. Destaca-se a seletividade para a formação de dois produtos, α-organiltio cetonas e α-organiltio ésteres, baseando-se na quantidade de base utilizada. Observou-se que quando utilizado 2 equivalentes de base a formação de α-organiltio cetonas é favorecida e quando utilizado 4 equivalentes de base os produtos α-organiltio ésteres são formados preferencialmente. Com isso, foi possível sintetizar dezesseis α-organiltio ésteres com rendimentos de 20 a 90%, e seis exemplos de de α-organiltio cetonas com rendimentos de 45 a 84%. Por fim, destaca-se a tolerância das reações a uma variedade de grupos com características doadoras e retiradoras de elétrons tais como metoxila, metila, trifluormetano, nitro e cloro em posições orto, meta e para.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESConselho 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/openAccessSais de Bunteα-organiltio carbonílicosβ-cetoésteresCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofreSynthesis of α-organilthio carbonyl compounds using bunte salts as a sulfur sourceinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisSchumacher, Ricardo Fredericohttp://lattes.cnpq.br/7856034546434135Silveira, Claudio da CruzRodrigues, Oscar Endrigo DornelesSperança, Adrianehttp://lattes.cnpq.br/1926230038499866Kazmierczak, Jean Carlo100600000000600600600600600600c0f45597-54e3-490c-9f9d-6888803e1a2adb0a48c4-6767-4e23-8b0c-f4734ee641e90b473614-8022-4c11-ba16-cfb6c339ab41d315e5ef-8c77-48c9-bc87-e90cab9c43e9a8c93a0e-d40b-4343-8cb7-456fc7cc0a70reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2020_KAZMIERCZAK _JEAN.pdfDIS_PPGQUIMICA_2020_KAZMIERCZAK _JEAN.pdfDissertaçãoapplication/pdf5517123http://repositorio.ufsm.br/bitstream/1/23519/1/DIS_PPGQUIMICA_2020_KAZMIERCZAK%20_JEAN.pdfc59687018c3582702b9260275ee1bdffMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
dc.title.alternative.eng.fl_str_mv Synthesis of α-organilthio carbonyl compounds using bunte salts as a sulfur source
title Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
spellingShingle Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
Kazmierczak, Jean Carlo
Sais de Bunte
α-organiltio carbonílicos
β-cetoésteres
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
title_full Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
title_fullStr Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
title_full_unstemmed Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
title_sort Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre
author Kazmierczak, Jean Carlo
author_facet Kazmierczak, Jean Carlo
author_role author
dc.contributor.advisor1.fl_str_mv Schumacher, Ricardo Frederico
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/7856034546434135
dc.contributor.advisor-co1.fl_str_mv Silveira, Claudio da Cruz
dc.contributor.referee1.fl_str_mv Rodrigues, Oscar Endrigo Dorneles
dc.contributor.referee2.fl_str_mv Sperança, Adriane
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/1926230038499866
dc.contributor.author.fl_str_mv Kazmierczak, Jean Carlo
contributor_str_mv Schumacher, Ricardo Frederico
Silveira, Claudio da Cruz
Rodrigues, Oscar Endrigo Dorneles
Sperança, Adriane
dc.subject.por.fl_str_mv Sais de Bunte
α-organiltio carbonílicos
β-cetoésteres
topic Sais de Bunte
α-organiltio carbonílicos
β-cetoésteres
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In this work, a series of α-organylthio carbonyl compounds were synthesizes from β-ketoesteres and Bunte salts, using NaOH as a reaction promoter in toluene at 100 ºC. The selectivity for the formation of two products, α-organylthio ketones and α-organylthio esters, is highlighted, based on the amount of base used. It was observed that when using 2 equivalents of base the formation of α-organylthio ketones is favored and when used 4 equivalents of base products α-organylthio esters are formed preferentially. Thus, it was possible to synthesize sixteen α-organylthio esters with yelds of 20 to 90% and six examples of α-organylthio ketones with yelds of 45 to 84%. Finally, the tolerance of reactions to a variety of groups with electron donating and withdrawing characteristics such as methoxy, methyl, trifluoromethane, nitro and chloro in ortho, meta and para positions is highlighted.
publishDate 2020
dc.date.issued.fl_str_mv 2020-02-21
dc.date.accessioned.fl_str_mv 2022-01-12T14:22:39Z
dc.date.available.fl_str_mv 2022-01-12T14:22:39Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/23519
url http://repositorio.ufsm.br/handle/1/23519
dc.language.iso.fl_str_mv por
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dc.relation.cnpq.fl_str_mv 100600000000
dc.relation.confidence.fl_str_mv 600
600
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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/
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rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
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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
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