The Strange Case of Sodium (S)-N-α-(Methylbenzyl)allylamide: Anion Rearrangement, Decomposition, and a Peculiar Propyl Addition

Emily C. Border, Magdaline Koutsaplis, Philip C. Andrews

Research output: Contribution to journalArticleOtherpeer-review

9 Citations (Scopus)


An unexpected aza-enolate propyl addition complex, [(PhC=CH2)(CH=C(CH2CH2CH3)CH3)NNa·THF] (1), was isolated when (S)-N-α-(methylbenzyl)allylamine reacted in hexane with nBuNa 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.

Original languageEnglish
Pages (from-to)303-305
Number of pages3
Issue number3
Publication statusPublished - 8 Feb 2016

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