ChemInform Abstract: Electrophilic Amination of C-H Acidic Compounds with 1-Oxa-2-azaspiro( 2.5)octane.
Abstract
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ChemInform Abstract
Reactions of the title spirooctane (II) with malonic (cf. (I), (IV)) and cyanoacetic acid derivatives (cf. (VI)) (13 examples in all) are investigated in detail. Several stabilization reactions after the primary amination step (introduction of a 1-hydroxycyclohexylamino group) are observed. Besides simple cyclohexanone eliminations (cf. ( III), (V)), an intramolecular nucleophilic attack to a nitrile group followed by a fast Dimroth rearrangement is one of the most important ones yielding diazaspirodecanones (cf. (VII)).
