Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane

Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed b...

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Detalhes bibliográficos
Autores: Barrionuevo, Cecilia Andrea, Schmidt, Luciana Carina, Argüello, Juan Elias
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2016
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositório:CONICET Digital (CONICET)
Idioma:inglês
OAI Identifier:oai:ri.conicet.gov.ar:11336/51621
Acesso em linha:http://hdl.handle.net/11336/51621
Access Level:Acceso aberto
Palavra-chave:1,4-Dicarbonyl Compounds
Ketone Enolate Anions
Dimerization
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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spelling Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropaneBarrionuevo, Cecilia AndreaSchmidt, Luciana CarinaArgüello, Juan Elias1,4-Dicarbonyl CompoundsKetone Enolate AnionsDimerizationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed by subsequent double alkylation with bis-iodide yielding a cyclopentane adduct. This methodology allows the use of a simple potassium tert-butoxide as a base at room temperature for the formation of three C–C bonds resulting in a relatively complex five-membered ring diketone structure under transition-metal-free conditions.Fil: Barrionuevo, Cecilia Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Schmidt, Luciana Carina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaRoyal Society of Chemistry2016-03-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/51621Barrionuevo, Cecilia Andrea; Schmidt, Luciana Carina; Argüello, Juan Elias; Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane; Royal Society of Chemistry; New Journal of Chemistry; 40; 5; 7-3-2016; 4550-45551144-05461369-9261CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2016/NJ/C5NJ03672Kinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C5NJ03672Kinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:34:31Zoai:ri.conicet.gov.ar:11336/51621instacron: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:34982024-05-08 13:34:31.668CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
title Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
spellingShingle Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
Barrionuevo, Cecilia Andrea
1,4-Dicarbonyl Compounds
Ketone Enolate Anions
Dimerization
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
title_full Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
title_fullStr Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
title_full_unstemmed Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
title_sort Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
dc.creator.none.fl_str_mv Barrionuevo, Cecilia Andrea
Schmidt, Luciana Carina
Argüello, Juan Elias
author Barrionuevo, Cecilia Andrea
author_facet Barrionuevo, Cecilia Andrea
Schmidt, Luciana Carina
Argüello, Juan Elias
author_role author
author2 Schmidt, Luciana Carina
Argüello, Juan Elias
author2_role author
author
dc.subject.none.fl_str_mv 1,4-Dicarbonyl Compounds
Ketone Enolate Anions
Dimerization
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic 1,4-Dicarbonyl Compounds
Ketone Enolate Anions
Dimerization
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed by subsequent double alkylation with bis-iodide yielding a cyclopentane adduct. This methodology allows the use of a simple potassium tert-butoxide as a base at room temperature for the formation of three C–C bonds resulting in a relatively complex five-membered ring diketone structure under transition-metal-free conditions.
publishDate 2016
dc.date.none.fl_str_mv 2016-03-07
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/11336/51621
Barrionuevo, Cecilia Andrea; Schmidt, Luciana Carina; Argüello, Juan Elias; Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane; Royal Society of Chemistry; New Journal of Chemistry; 40; 5; 7-3-2016; 4550-4555
1144-0546
1369-9261
CONICET Digital
CONICET
url http://hdl.handle.net/11336/51621
identifier_str_mv Barrionuevo, Cecilia Andrea; Schmidt, Luciana Carina; Argüello, Juan Elias; Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane; Royal Society of Chemistry; New Journal of Chemistry; 40; 5; 7-3-2016; 4550-4555
1144-0546
1369-9261
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2016/NJ/C5NJ03672K
info:eu-repo/semantics/altIdentifier/doi/10.1039/C5NJ03672K
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15,811543

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