INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE

Detalhes bibliográficos
Autor(a) principal: Vieira, Vanessa B.
Data de Publicação: 2020
Outros Autores: Silva, Eliada A. da, Carvalho Jr, Valdemiro P. [UNESP], Lima-Neto, Benedito S., Sa, Jose L. S.
Tipo de documento: Artigo
Idioma: por
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.21577/0100-4042.20170462
http://hdl.handle.net/11449/195260
Resumo: Cinnamyl alcohol (AC) and cinnamyl acetate (ACM) were used as substrates in olefin metathesis reactions catalyzed by RuCl2(PCy3)(2)(=CHPh), first-generation Grubbs catalyst-G1, and RuCl2(PCy3)(H(2)Mes)(= CHPh), second-generation Grubbs catalyst-G2. The reactions occurred in the same reaction conditions for both substrates, 50 degrees C, for 24 h, in the proportions Ru:substrate of 1:1 and 1:10 mol. At the end of each experiment, the reaction mixture was evaluated by GC-MS and NMR of C-13[H-1]. The results revealed different products when G1 and G2 are applied in the metathesis of AC, 1,5-diphenyl-2-pentene and stilbene, respectively. When ACM is the substrate, no product is noted with G1 and stilbene was the compound obtained with G2 as catalyst. In this study, we have presented a discussion about the electronic and steric influence of the ancillary ligands in the yield and type of product formed in the catalytic process.
id UNSP_550139c04dc16b61ee02134e75cc062f
oai_identifier_str oai:repositorio.unesp.br:11449/195260
network_acronym_str UNSP
network_name_str Repositório Institucional da UNESP
repository_id_str 2946
spelling INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATEolefin metathesisGrubbs catalystscinnamic groupsCinnamyl alcohol (AC) and cinnamyl acetate (ACM) were used as substrates in olefin metathesis reactions catalyzed by RuCl2(PCy3)(2)(=CHPh), first-generation Grubbs catalyst-G1, and RuCl2(PCy3)(H(2)Mes)(= CHPh), second-generation Grubbs catalyst-G2. The reactions occurred in the same reaction conditions for both substrates, 50 degrees C, for 24 h, in the proportions Ru:substrate of 1:1 and 1:10 mol. At the end of each experiment, the reaction mixture was evaluated by GC-MS and NMR of C-13[H-1]. The results revealed different products when G1 and G2 are applied in the metathesis of AC, 1,5-diphenyl-2-pentene and stilbene, respectively. When ACM is the substrate, no product is noted with G1 and stilbene was the compound obtained with G2 as catalyst. In this study, we have presented a discussion about the electronic and steric influence of the ancillary ligands in the yield and type of product formed in the catalytic process.Univ Estadual Piaui, Ctr Ciencias Nat, BR-64002150 Teresina, PI, BrazilUniv Sao Paulo, Inst Quim Sao Carlos, BR-13560097 Sao Carlos, SP, BrazilUniv Estadual Paulista, Fac Ciencias & Tecnol, BR-19060900 Presidente Prudente, SP, BrazilUniv Estadual Paulista, Fac Ciencias & Tecnol, BR-19060900 Presidente Prudente, SP, BrazilSoc Brasileira QuimicaUniv Estadual PiauiUniversidade de São Paulo (USP)Universidade Estadual Paulista (Unesp)Vieira, Vanessa B.Silva, Eliada A. daCarvalho Jr, Valdemiro P. [UNESP]Lima-Neto, Benedito S.Sa, Jose L. S.2020-12-10T17:28:43Z2020-12-10T17:28:43Z2020-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article24-31application/pdfhttp://dx.doi.org/10.21577/0100-4042.20170462Quimica Nova. Sao Paulo: Soc Brasileira Quimica, v. 43, n. 1, p. 24-31, 2020.0100-4042http://hdl.handle.net/11449/19526010.21577/0100-4042.20170462S0100-40422020000100024WOS:000520600700004S0100-40422020000100024.pdfWeb of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPporQuimica Novainfo:eu-repo/semantics/openAccess2023-10-06T06:02:11Zoai:repositorio.unesp.br:11449/195260Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T14:07:56.053199Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
title INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
spellingShingle INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
Vieira, Vanessa B.
olefin metathesis
Grubbs catalysts
cinnamic groups
title_short INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
title_full INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
title_fullStr INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
title_full_unstemmed INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
title_sort INFLUENCE OF THE STERIC HINDRANCE OF ANCILLARY LIGANDS IN Ru-BASED COMPLEXES APPLIED IN METATHESIS OF CINNAMYL ALCOHOL AND CINNAMYL ACETATE
author Vieira, Vanessa B.
author_facet Vieira, Vanessa B.
Silva, Eliada A. da
Carvalho Jr, Valdemiro P. [UNESP]
Lima-Neto, Benedito S.
Sa, Jose L. S.
author_role author
author2 Silva, Eliada A. da
Carvalho Jr, Valdemiro P. [UNESP]
Lima-Neto, Benedito S.
Sa, Jose L. S.
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Univ Estadual Piaui
Universidade de São Paulo (USP)
Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Vieira, Vanessa B.
Silva, Eliada A. da
Carvalho Jr, Valdemiro P. [UNESP]
Lima-Neto, Benedito S.
Sa, Jose L. S.
dc.subject.por.fl_str_mv olefin metathesis
Grubbs catalysts
cinnamic groups
topic olefin metathesis
Grubbs catalysts
cinnamic groups
description Cinnamyl alcohol (AC) and cinnamyl acetate (ACM) were used as substrates in olefin metathesis reactions catalyzed by RuCl2(PCy3)(2)(=CHPh), first-generation Grubbs catalyst-G1, and RuCl2(PCy3)(H(2)Mes)(= CHPh), second-generation Grubbs catalyst-G2. The reactions occurred in the same reaction conditions for both substrates, 50 degrees C, for 24 h, in the proportions Ru:substrate of 1:1 and 1:10 mol. At the end of each experiment, the reaction mixture was evaluated by GC-MS and NMR of C-13[H-1]. The results revealed different products when G1 and G2 are applied in the metathesis of AC, 1,5-diphenyl-2-pentene and stilbene, respectively. When ACM is the substrate, no product is noted with G1 and stilbene was the compound obtained with G2 as catalyst. In this study, we have presented a discussion about the electronic and steric influence of the ancillary ligands in the yield and type of product formed in the catalytic process.
publishDate 2020
dc.date.none.fl_str_mv 2020-12-10T17:28:43Z
2020-12-10T17:28:43Z
2020-01-01
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.21577/0100-4042.20170462
Quimica Nova. Sao Paulo: Soc Brasileira Quimica, v. 43, n. 1, p. 24-31, 2020.
0100-4042
http://hdl.handle.net/11449/195260
10.21577/0100-4042.20170462
S0100-40422020000100024
WOS:000520600700004
S0100-40422020000100024.pdf
url http://dx.doi.org/10.21577/0100-4042.20170462
http://hdl.handle.net/11449/195260
identifier_str_mv Quimica Nova. Sao Paulo: Soc Brasileira Quimica, v. 43, n. 1, p. 24-31, 2020.
0100-4042
10.21577/0100-4042.20170462
S0100-40422020000100024
WOS:000520600700004
S0100-40422020000100024.pdf
dc.language.iso.fl_str_mv por
language por
dc.relation.none.fl_str_mv Quimica Nova
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 24-31
application/pdf
dc.publisher.none.fl_str_mv Soc Brasileira Quimica
publisher.none.fl_str_mv Soc Brasileira Quimica
dc.source.none.fl_str_mv Web of Science
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
_version_ 1808128320259227648