Hydricity-Promoted [1,5]-H Shifts in Acetalic Ketenimines and Carbodiimides

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 computation...

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Bibliographic Details
Published in:Organic letters 2006-11, Vol.8 (24), p.5645-5648
Main Authors: Alajarín, Mateo, Bonillo, Baltasar, Ortín, María-Mar, Sánchez-Andrada, Pilar, Vidal, Ángel
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062373w