Exploring Interrupted Nazarov Cyclizations Using Tethered Sulfonamide Nucleophiles: Insights into Capture Pathways.

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