Ketenes are among the most reactive alkenes, and are known in certain cases to react with tertiary amines such as triethylamine forming observable zwitterionic intermediates that  lead to amides of dialkylamines (Fig. 1). Our studies of the mechanisms of these processes reveal that conventional 1,6-intramolecular eliminations are not sufficient to explain formation of these products. Possible pathways for these reactions will be presented.

Enigmatic reactions of ketenes with <i>tertiary</i>-amines

243rd National Meeting (2012)

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Enigmatic reactions of ketenes with tertiary-amines