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

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.

SUBMITTER: Milosavljevic A 

PROVIDER: S-EPMC11634052 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature