4.7 Article

NHC-Stabilized 1-Hydro-1H-borole and Its Nondegenerate Sigmatropic Isomers

Journal

INORGANIC CHEMISTRY
Volume 50, Issue 10, Pages 4247-4249

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ic200533e

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Funding

  1. Alexander von Humboldt Foundation

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Electrophilic quenching of a carbene-stabilized pi-boryl anion with the Bronsted acid Et3NHCl provides a convenient synthetic route to the parent NHC-stabilized 1-hydroborole, which isomerizes to the corresponding 3-hydroborole via two successive nondegenerate [1,5]-sigmatropic hydrogen migrations. Molecular structures of both isomers have been determined by X-ray crystallography.

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