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Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition.
Gunawardene, Praveen N; Luo, Wilson; Polgar, Alexander M; Corrigan, John F; Workentin, Mark S.
Afiliação
  • Gunawardene PN; Department of Chemistry and the Centre for Materials and Biomaterials Research , The University of Western Ontario , Richmond Street , London , Ontario N6A 5B7 , Canada.
  • Luo W; Department of Chemistry and the Centre for Materials and Biomaterials Research , The University of Western Ontario , Richmond Street , London , Ontario N6A 5B7 , Canada.
  • Polgar AM; Department of Chemistry and the Centre for Materials and Biomaterials Research , The University of Western Ontario , Richmond Street , London , Ontario N6A 5B7 , Canada.
  • Corrigan JF; Department of Chemistry and the Centre for Materials and Biomaterials Research , The University of Western Ontario , Richmond Street , London , Ontario N6A 5B7 , Canada.
  • Workentin MS; Department of Chemistry and the Centre for Materials and Biomaterials Research , The University of Western Ontario , Richmond Street , London , Ontario N6A 5B7 , Canada.
Org Lett ; 21(14): 5547-5551, 2019 Jul 19.
Article em En | MEDLINE | ID: mdl-31251633
ABSTRACT
Highly accelerated inverse-electron-demand strain-promoted alkyne-nitrone cycloaddition (IED SPANC) between a stable cyclooctyne (bicyclo[6.1.0]nonyne (BCN)) and nitrones delocalized into a Cα-pyridinium functionality is reported, with the most electron-deficient "pyridinium-nitrone" displaying among the most rapid cycloadditions to BCN that is currently reported. Density functional theory (DFT) and X-ray crystallography are explored to rationalize the effects of N- and Cα-substituent modifications at the nitrone on IED SPANC reaction kinetics and the overall rapid reactivity of pyridinium-delocalized nitrones.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Ano de publicação: 2019 Tipo de documento: Article
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Ano de publicação: 2019 Tipo de documento: Article