Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts

Detalhes bibliográficos
Autor(a) principal: Stefani, Helio A. [UNIFESP]
Data de Publicação: 2008
Outros Autores: Guadagnin, Rafael C., Keppler, Artur F., Botteselle, Giancarlo V., Comasseto, Joao V., Suganuma, Carlos A.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNIFESP
Texto Completo: http://repositorio.unifesp.br/handle/11600/30442
http://dx.doi.org/10.1186/1860-5397-4-9
Resumo: Through direct transmetalation reaction of Z-vinylic tellurides with nBuLi was observed the unexpected isomerization of double bonds leading to potassium E-vinyltrifluoroborates salts in low to moderate yields. Using EPR spin trapping experiments the radical species that promoted the stereoinversion of Z-vinylic organometallic species during the preparation of potassium vinyltrifluoroborate salts was identified. the experiments support the proposed mechanism, which is based on the homolytic cleavage of the TenBu bond.
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spelling Stefani, Helio A. [UNIFESP]Guadagnin, Rafael C.Keppler, Artur F.Botteselle, Giancarlo V.Comasseto, Joao V.Suganuma, Carlos A.Universidade de São Paulo (USP)Universidade Federal de São Paulo (UNIFESP)2016-01-24T13:49:34Z2016-01-24T13:49:34Z2008-02-05Beilstein Journal of Organic Chemistry. Frankfurt Am Main: Beilstein-institut, v. 4, 4 p., 2008.1860-5397http://repositorio.unifesp.br/handle/11600/30442http://dx.doi.org/10.1186/1860-5397-4-9WOS000253207700001.pdf10.1186/1860-5397-4-9WOS:000253207700001Through direct transmetalation reaction of Z-vinylic tellurides with nBuLi was observed the unexpected isomerization of double bonds leading to potassium E-vinyltrifluoroborates salts in low to moderate yields. Using EPR spin trapping experiments the radical species that promoted the stereoinversion of Z-vinylic organometallic species during the preparation of potassium vinyltrifluoroborate salts was identified. the experiments support the proposed mechanism, which is based on the homolytic cleavage of the TenBu bond.Univ São Paulo, Fac Ciencias Farmaceut, São Paulo, BrazilUniversidade Federal de São Paulo, Dept Biofis, São Paulo, BrazilUniv São Paulo, Inst Quim, São Paulo, BrazilUniversidade Federal de São Paulo, Dept Biofis, São Paulo, BrazilWeb of Science4engBeilstein-institutBeilstein Journal of Organic ChemistryMechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate saltsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESPORIGINALWOS000253207700001.pdfapplication/pdf363495${dspace.ui.url}/bitstream/11600/30442/1/WOS000253207700001.pdf73a0dd615d5e727afaaba7d21063eee8MD51open accessTEXTWOS000253207700001.pdf.txtWOS000253207700001.pdf.txtExtracted texttext/plain14515${dspace.ui.url}/bitstream/11600/30442/2/WOS000253207700001.pdf.txt884a5862b1beda465cf5904331c58efcMD52open access11600/304422023-02-15 10:56:36.562open accessoai:repositorio.unifesp.br:11600/30442Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestopendoar:34652023-02-15T13:56:36Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.en.fl_str_mv Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
spellingShingle Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
Stefani, Helio A. [UNIFESP]
title_short Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_full Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_fullStr Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_full_unstemmed Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_sort Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
author Stefani, Helio A. [UNIFESP]
author_facet Stefani, Helio A. [UNIFESP]
Guadagnin, Rafael C.
Keppler, Artur F.
Botteselle, Giancarlo V.
Comasseto, Joao V.
Suganuma, Carlos A.
author_role author
author2 Guadagnin, Rafael C.
Keppler, Artur F.
Botteselle, Giancarlo V.
Comasseto, Joao V.
Suganuma, Carlos A.
author2_role author
author
author
author
author
dc.contributor.institution.none.fl_str_mv Universidade de São Paulo (USP)
Universidade Federal de São Paulo (UNIFESP)
dc.contributor.author.fl_str_mv Stefani, Helio A. [UNIFESP]
Guadagnin, Rafael C.
Keppler, Artur F.
Botteselle, Giancarlo V.
Comasseto, Joao V.
Suganuma, Carlos A.
description Through direct transmetalation reaction of Z-vinylic tellurides with nBuLi was observed the unexpected isomerization of double bonds leading to potassium E-vinyltrifluoroborates salts in low to moderate yields. Using EPR spin trapping experiments the radical species that promoted the stereoinversion of Z-vinylic organometallic species during the preparation of potassium vinyltrifluoroborate salts was identified. the experiments support the proposed mechanism, which is based on the homolytic cleavage of the TenBu bond.
publishDate 2008
dc.date.issued.fl_str_mv 2008-02-05
dc.date.accessioned.fl_str_mv 2016-01-24T13:49:34Z
dc.date.available.fl_str_mv 2016-01-24T13:49:34Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv Beilstein Journal of Organic Chemistry. Frankfurt Am Main: Beilstein-institut, v. 4, 4 p., 2008.
dc.identifier.uri.fl_str_mv http://repositorio.unifesp.br/handle/11600/30442
http://dx.doi.org/10.1186/1860-5397-4-9
dc.identifier.issn.none.fl_str_mv 1860-5397
dc.identifier.file.none.fl_str_mv WOS000253207700001.pdf
dc.identifier.doi.none.fl_str_mv 10.1186/1860-5397-4-9
dc.identifier.wos.none.fl_str_mv WOS:000253207700001
identifier_str_mv Beilstein Journal of Organic Chemistry. Frankfurt Am Main: Beilstein-institut, v. 4, 4 p., 2008.
1860-5397
WOS000253207700001.pdf
10.1186/1860-5397-4-9
WOS:000253207700001
url http://repositorio.unifesp.br/handle/11600/30442
http://dx.doi.org/10.1186/1860-5397-4-9
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartof.none.fl_str_mv Beilstein Journal of Organic Chemistry
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dc.publisher.none.fl_str_mv Beilstein-institut
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dc.source.none.fl_str_mv reponame:Repositório Institucional da UNIFESP
instname:Universidade Federal de São Paulo (UNIFESP)
instacron:UNIFESP
instname_str Universidade Federal de São Paulo (UNIFESP)
instacron_str UNIFESP
institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
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