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

Electron-donating iminophosphoranes were found to significantly enhance 4 pi-ring opening of benzocyclobutenes to generate o-quinodimethanes at 20-25 degrees C. These iminophosphorane benzocyclobutenes can be conveniently generated from azide benzocyclobutenes and phosphines via the Staudinger reaction. Thus, Staudinger reactiontriggered 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.