Abstract
This manuscript describes a study of diverse reaction outcomes that stem from the ionization of aza‐alkynyl‐Prins adducts. Experimental results have demonstrated unexpected behavior in the nitrogen‐containing systems compared to the analogous oxygen derivatives derived from oxa‐Prins/halo‐Nazarov sequences. In‐depth experimental studies and computational analysis revealed an intricate mechanism involving competing halo‐Nazarov and imino‐Nazarov pathways. These findings further elucidate the reaction chemistry of 3‐halo‐pentadienyl cation intermediates, and expand their utility in synthetic transformations.
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