By using N-acyliminium ion chemistry, several ω-propadienyllactams and a propadienyloxazolidine were prepared from N-acyliminium ion precursors and propargylsilanes. Treatment of these allene containing lactams and oxazolidinone with allyl halides or an allyl carbonate using Pd (II)-salts as the catalyst gave rise to a coupling– cyclization reaction, yielding bicyclic systems in which the allyl moiety is incorporated. ...