Organic Letters p. 5645 - 5648 (2006)
Update date:2022-08-02
Topics:
Alajarin, Mateo
Bonillo, Baltasar
Ortin, Maria-Mar
Sanchez-Andrada, Pilar
Vidal, Angel
2-Monosubstituted 1,3-dioxolanes and dithiolanes act as hydride-releasing fragments, transferring intramolecularly their acetalic H atom to the central carbon of ketenimine functions. The presumed products of these migrations, o-quinomethanimines, undergo in situ 6π-electrocyclization. A computational study supports this mechanism and the hydride-shift character of the first step. Carbodiimides were also suitable substrates, although less reactive.
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(2006)