Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates

Detalhes bibliográficos
Autor(a) principal: Pinho e Melo, Teresa M. V. D.
Data de Publicação: 2003
Outros Autores: Cardoso, Ana L., Gonsalves, António M. d'A. Rocha
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/5167
https://doi.org/10.1016/s0040-4020(03)00248-5
Resumo: The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobornyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobornyl acetate.
id RCAP_785bdc8b8c52f579616b29d806192f65
oai_identifier_str oai:estudogeral.uc.pt:10316/5167
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylatesdehalogenation2-halo-2H-azirine-2-carboxylateschiral 2H-azirine-2-carboxylatesThe dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobornyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobornyl acetate.http://www.sciencedirect.com/science/article/B6THR-482NK06-7/1/b576da25bb07c16918052295f89735c82003info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleaplication/PDFhttp://hdl.handle.net/10316/5167http://hdl.handle.net/10316/5167https://doi.org/10.1016/s0040-4020(03)00248-5engTetrahedron. 59:13 (2003) 2345-2351Pinho e Melo, Teresa M. V. D.Cardoso, Ana L.Gonsalves, António M. d'A. Rochainfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2021-09-02T11:12:30Zoai:estudogeral.uc.pt:10316/5167Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:20.256993Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
title Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
spellingShingle Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
Pinho e Melo, Teresa M. V. D.
dehalogenation
2-halo-2H-azirine-2-carboxylates
chiral 2H-azirine-2-carboxylates
title_short Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
title_full Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
title_fullStr Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
title_full_unstemmed Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
title_sort Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
author Pinho e Melo, Teresa M. V. D.
author_facet Pinho e Melo, Teresa M. V. D.
Cardoso, Ana L.
Gonsalves, António M. d'A. Rocha
author_role author
author2 Cardoso, Ana L.
Gonsalves, António M. d'A. Rocha
author2_role author
author
dc.contributor.author.fl_str_mv Pinho e Melo, Teresa M. V. D.
Cardoso, Ana L.
Gonsalves, António M. d'A. Rocha
dc.subject.por.fl_str_mv dehalogenation
2-halo-2H-azirine-2-carboxylates
chiral 2H-azirine-2-carboxylates
topic dehalogenation
2-halo-2H-azirine-2-carboxylates
chiral 2H-azirine-2-carboxylates
description The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobornyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobornyl acetate.
publishDate 2003
dc.date.none.fl_str_mv 2003
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://hdl.handle.net/10316/5167
http://hdl.handle.net/10316/5167
https://doi.org/10.1016/s0040-4020(03)00248-5
url http://hdl.handle.net/10316/5167
https://doi.org/10.1016/s0040-4020(03)00248-5
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Tetrahedron. 59:13 (2003) 2345-2351
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv aplication/PDF
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
_version_ 1799133905253564416

Registros relacionados