Diazo Esters as Dienophiles in Intramolecular (4 + 2) Cycloadditions: Computational Explorations of Mechanism.
The first experimental examples of Diels-Alder (DA) reactions of diazo compounds as heterodienophiles with dienes have been studied with density functional theory (DFT) using the M06-2X functional. For comparison, the reactivities of diazo esters as dienophiles or 1,3-dipoles with 1,3-dienes in inte...
| Publicado en: | Journal of the American Chemical Society Vol. 139; no. 7; pp. 2766 - 2771 |
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| Autores principales: | , , , , , , |
| Formato: | Artículo |
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American Chemical Society
2/22/2017
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=123637678&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 123637678 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 2/22/2017 vid: 139 iid: 7 pid: 997 pub: American Chemical Society artinfo: ui: 123637678 10.1021/jacs.6b12371 ppf: 2766 ppct: 5 formats: tig: atl: Diazo Esters as Dienophiles in Intramolecular (4 + 2) Cycloadditions: Computational Explorations of Mechanism. aug: au: Abing Duan Peiyuan Yu Fang Liu Huang Qiu Feng Long Gu Doyle, Michael P. Houk, K. N. affil: Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education; School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States su: Diazo compounds Ring formation (Chemistry) Diels-Alder reaction Dienophiles Density functional theory sug: subj: Diazo compounds Ring formation (Chemistry) Diels-Alder reaction Dienophiles Density functional theory ab: The first experimental examples of Diels-Alder (DA) reactions of diazo compounds as heterodienophiles with dienes have been studied with density functional theory (DFT) using the M06-2X functional. For comparison, the reactivities of diazo esters as dienophiles or 1,3-dipoles with 1,3-dienes in intermolecular model systems have been analyzed by the distortion/interaction model. The 1,3-dipolar cycloaddition is strongly favored for the intermolecular system. The intramolecular example is unique because the tether strongly favors the (4 + 2) cycloaddition. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2017 holdings: @attributes: islocal: N |
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