Synthesis of Organotin Substituted Tricyclic Macrodiolides

Autores
Zacconi, Flavia C.; Ocampo, Romina Andrea; Podestá, Julio Cesar; Koll, Liliana Cristina
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The radical addition of triorganotin hydrides, R3SnH (R=n-butyl, phenyl, neophyltin), to four unsaturated diesters of (11R,12R)-9,10-dihydro-9,10-ethaneanthracene-11,12-dimethanol leads to products of cyclohydrostannation with an average yield of around 80%. Whereas the addition of these hydrides to diacrylate and dimethacrylate leads to the expected mixtures containing two and four distereoisomeric cyclized products respectively, the addition to di-2-methyl- and di-2-phenylcinnamate yields only four out of the sixteen possible stereoisomers. The observed high stereoselectivity is consistent with a radical tandem cyclohydrostannation mechanism. Full proton (1H), carbon 13 (13C) and tin 119 (119Sn) nuclear magnetic resonance (NMR) data are given.
Fil: Zacconi, Flavia C.. Pontificia Universidad Católica de Chile. Facultad de Química; Chile
Fil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Materia
ORGANOTIN SUBSTITUED MACRODIOLIDES
CYCLOHYDROSTANNATION
STEREOSELECTIVE TANDEM CYCLIZATION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/4656
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of Organotin Substituted Tricyclic MacrodiolidesZacconi, Flavia C.Ocampo, Romina AndreaPodestá, Julio CesarKoll, Liliana CristinaORGANOTIN SUBSTITUED MACRODIOLIDESCYCLOHYDROSTANNATIONSTEREOSELECTIVE TANDEM CYCLIZATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The radical addition of triorganotin hydrides, R3SnH (R=n-butyl, phenyl, neophyltin), to four unsaturated diesters of (11R,12R)-9,10-dihydro-9,10-ethaneanthracene-11,12-dimethanol leads to products of cyclohydrostannation with an average yield of around 80%. Whereas the addition of these hydrides to diacrylate and dimethacrylate leads to the expected mixtures containing two and four distereoisomeric cyclized products respectively, the addition to di-2-methyl- and di-2-phenylcinnamate yields only four out of the sixteen possible stereoisomers. The observed high stereoselectivity is consistent with a radical tandem cyclohydrostannation mechanism. Full proton (1H), carbon 13 (13C) and tin 119 (119Sn) nuclear magnetic resonance (NMR) data are given.Fil: Zacconi, Flavia C.. Pontificia Universidad Católica de Chile. Facultad de Química; ChileFil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur; ArgentinaFil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; ArgentinaFil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; ArgentinaSociedade Brasileira de Química2015-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/4656Zacconi, Flavia C.; Ocampo, Romina Andrea; Podestá, Julio Cesar; Koll, Liliana Cristina; Synthesis of Organotin Substituted Tricyclic Macrodiolides; Sociedade Brasileira de Química; Journal Of The Brazilian Chemical Society; 27; 3; 10-2015; 484-4920103-50531678-4790enginfo:eu-repo/semantics/altIdentifier/doi/10.5935/0103-5053.20150275info:eu-repo/semantics/altIdentifier/issn/0103-5053info:eu-repo/semantics/altIdentifier/url/http://jbcs.sbq.org.br/imagebank/pdf/v27n3a03.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:00:23Zoai:ri.conicet.gov.ar:11336/4656instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:00:23.902CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Organotin Substituted Tricyclic Macrodiolides
title Synthesis of Organotin Substituted Tricyclic Macrodiolides
spellingShingle Synthesis of Organotin Substituted Tricyclic Macrodiolides
Zacconi, Flavia C.
ORGANOTIN SUBSTITUED MACRODIOLIDES
CYCLOHYDROSTANNATION
STEREOSELECTIVE TANDEM CYCLIZATION
title_short Synthesis of Organotin Substituted Tricyclic Macrodiolides
title_full Synthesis of Organotin Substituted Tricyclic Macrodiolides
title_fullStr Synthesis of Organotin Substituted Tricyclic Macrodiolides
title_full_unstemmed Synthesis of Organotin Substituted Tricyclic Macrodiolides
title_sort Synthesis of Organotin Substituted Tricyclic Macrodiolides
dc.creator.none.fl_str_mv Zacconi, Flavia C.
Ocampo, Romina Andrea
Podestá, Julio Cesar
Koll, Liliana Cristina
author Zacconi, Flavia C.
author_facet Zacconi, Flavia C.
Ocampo, Romina Andrea
Podestá, Julio Cesar
Koll, Liliana Cristina
author_role author
author2 Ocampo, Romina Andrea
Podestá, Julio Cesar
Koll, Liliana Cristina
author2_role author
author
author
dc.subject.none.fl_str_mv ORGANOTIN SUBSTITUED MACRODIOLIDES
CYCLOHYDROSTANNATION
STEREOSELECTIVE TANDEM CYCLIZATION
topic ORGANOTIN SUBSTITUED MACRODIOLIDES
CYCLOHYDROSTANNATION
STEREOSELECTIVE TANDEM CYCLIZATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The radical addition of triorganotin hydrides, R3SnH (R=n-butyl, phenyl, neophyltin), to four unsaturated diesters of (11R,12R)-9,10-dihydro-9,10-ethaneanthracene-11,12-dimethanol leads to products of cyclohydrostannation with an average yield of around 80%. Whereas the addition of these hydrides to diacrylate and dimethacrylate leads to the expected mixtures containing two and four distereoisomeric cyclized products respectively, the addition to di-2-methyl- and di-2-phenylcinnamate yields only four out of the sixteen possible stereoisomers. The observed high stereoselectivity is consistent with a radical tandem cyclohydrostannation mechanism. Full proton (1H), carbon 13 (13C) and tin 119 (119Sn) nuclear magnetic resonance (NMR) data are given.
Fil: Zacconi, Flavia C.. Pontificia Universidad Católica de Chile. Facultad de Química; Chile
Fil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
description The radical addition of triorganotin hydrides, R3SnH (R=n-butyl, phenyl, neophyltin), to four unsaturated diesters of (11R,12R)-9,10-dihydro-9,10-ethaneanthracene-11,12-dimethanol leads to products of cyclohydrostannation with an average yield of around 80%. Whereas the addition of these hydrides to diacrylate and dimethacrylate leads to the expected mixtures containing two and four distereoisomeric cyclized products respectively, the addition to di-2-methyl- and di-2-phenylcinnamate yields only four out of the sixteen possible stereoisomers. The observed high stereoselectivity is consistent with a radical tandem cyclohydrostannation mechanism. Full proton (1H), carbon 13 (13C) and tin 119 (119Sn) nuclear magnetic resonance (NMR) data are given.
publishDate 2015
dc.date.none.fl_str_mv 2015-10
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/4656
Zacconi, Flavia C.; Ocampo, Romina Andrea; Podestá, Julio Cesar; Koll, Liliana Cristina; Synthesis of Organotin Substituted Tricyclic Macrodiolides; Sociedade Brasileira de Química; Journal Of The Brazilian Chemical Society; 27; 3; 10-2015; 484-492
0103-5053
1678-4790
url http://hdl.handle.net/11336/4656
identifier_str_mv Zacconi, Flavia C.; Ocampo, Romina Andrea; Podestá, Julio Cesar; Koll, Liliana Cristina; Synthesis of Organotin Substituted Tricyclic Macrodiolides; Sociedade Brasileira de Química; Journal Of The Brazilian Chemical Society; 27; 3; 10-2015; 484-492
0103-5053
1678-4790
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.5935/0103-5053.20150275
info:eu-repo/semantics/altIdentifier/issn/0103-5053
info:eu-repo/semantics/altIdentifier/url/http://jbcs.sbq.org.br/imagebank/pdf/v27n3a03.pdf
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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