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Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature

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Abstract

Electron-donating iminophosphoranes were found to significantly enhance 4π-ring opening of benzocyclobutenes to generate o-quinodimethanes at 20–25 °C. These iminophosphorane benzocyclobutenes can be conveniently generated from azide benzocyclobutenes and phosphines via the Staudinger reaction. Thus, Staudinger reaction-triggered sequential molecular transformations of the azide benzocyclobutenes have been established via o-quinodimethanes at ambient temperature, which is expected to exhibit potential for a wide range of applications.

Graphical abstract: Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature

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Publication details

The article was received on 28 Feb 2019, accepted on 29 Apr 2019 and first published on 30 Apr 2019


Article type: Communication
DOI: 10.1039/C9CC01679A
Chem. Commun., 2019, Advance Article

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    Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature

    A. Kohyama, E. Koresawa, K. Tsuge and Y. Matsuya, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC01679A

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