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https://hdl.handle.net/1822/3111
Registo completo
Campo DC | Valor | Idioma |
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dc.contributor.author | Esteves, Ana Paula | - |
dc.contributor.author | Goken, Danielle M. | - |
dc.contributor.author | Klein, Lee J. | - |
dc.contributor.author | Lemos, Maria A. | - |
dc.contributor.author | Medeiros, Maria José | - |
dc.contributor.author | Peters, Dennis G. | - |
dc.date.accessioned | 2005-09-30T12:28:06Z | - |
dc.date.available | 2005-09-30T12:28:06Z | - |
dc.date.issued | 2003 | - |
dc.identifier.citation | "The Journal of Organic Chemistry". ISSN 0022-3263. 68 (2003) 1024-1029. | eng |
dc.identifier.issn | 0022-3263 | eng |
dc.identifier.uri | https://hdl.handle.net/1822/3111 | - |
dc.description.abstract | Cyclic voltammetry and controlled-potential electrolysis have been employed to investigate and characterize the reductive intramolecular cyclization of ethyl 2-bromo-3-(3′,4′-dimethoxyphenyl)-3-propargyloxy-propanoate (1) promoted by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane)nickel(I), [Ni(tmc)]+, electrogenerated at glassy carbon cathodes in dimethylformamide containing tetraalkylammonium salts. Cyclic voltammograms for reduction of [Ni(tmc)]2+ in the presence of 1 reveal that [Ni(tmc)]+ catalytically reduces 1 at potentials more positive than those required for direct reduction of 1. During controlled-potential electrolyses of solutions containing [Ni(tmc)]2+ and 1, catalytic reduction of the latter proceeds via one-electron cleavage of the carbon–bromine bond to form a radical intermediate that undergoes cyclization to afford 2-(3′,4′-dimethoxyphenyl-3-ethoxycarbonyl-4-methylene-tetrahydrofuran (2). In the presence of a base (either electrogenerated or deliberately added as potassium tert-butoxide), 2 rearranges to give 2-(3′,4′-dimethoxyphenyl-3-ethoxycarbonyl-4-methyl-2,5-dihydrofuran (3). A mechanistic scheme is proposed to explain the results obtained by means of cyclic voltammetry and controlled-potential electrolysis. | eng |
dc.description.sponsorship | Fundação Calouste Gulbenkian. | por |
dc.language.iso | eng | eng |
dc.publisher | American Chemical Society | por |
dc.rights | restrictedAccess | eng |
dc.subject | Cyclization | eng |
dc.subject | Radical | eng |
dc.title | Electroreductive intramolecular cyclization of a bromo propargyloxy ester catalyzed by nickel(I) tetramethylcyclam electrogenerated at carbon cathodes in dimethylformamide | eng |
dc.type | article | eng |
dc.peerreviewed | yes | eng |
sdum.pagination | 1024-1029 | eng |
sdum.publicationstatus | published | eng |
sdum.volume | 68 | eng |
oaire.citationStartPage | 1024 | por |
oaire.citationEndPage | 1029 | por |
oaire.citationIssue | 3 | por |
oaire.citationVolume | 68 | por |
dc.identifier.doi | 10.1021/jo026102k | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | The Journal of Organic Chemistry | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Maria Medeiros-paperJOC.pdf Acesso restrito! | Documento principal | 105,74 kB | Adobe PDF | Ver/Abrir |