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Exploring Interrupted Nazarov Cyclizations Using Tethered Sulfonamide Nucleophiles: Insights into Capture Pathways
Aleksa Milosavljevic1, Jackson J Hernandez1, Patrycia K Zybura1
1Department of Chemistry, University of Rochester, Rochester, NY 14627.
None:
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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