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

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...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2019-05, Vol.55 (44), p.6205-6208
Hauptverfasser: Kohyama, Aki, Koresawa, Eri, Tsuge, Kiyoshi, Matsuya, Yuji
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Sprache:eng
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc01679a