An unexpected aza-enolate propyl addition complex, [(PhC═CH 2 )(CH═C(CH 2 CH 2 CH 3 )CH 3 )NNa·THF] ∞ ( 1 ), was isolated when ( S )- N -α-(methylbenzyl)allylamine reacted in hexane with n BuNa in the presence of THF. Analytical studies revealed a decomposition of the sodium 1-azaallylamide to a sodium enamide and propene, identified by solution studies and a GC-headspace study, respectively. Propene then adds to the carbanion tautomer of the sodium 1-azaallylamide followed by anionic rearrangements to later form the aza-enolate propyl addition complex.
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Border et al. (2016) studied this question.
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