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Brønsted Acids Enable Three Molecular Rearrangements of One 3‑Alkylidene‑2H‑1,2-oxazine Molecule into Distinct Heterocyles

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journal contribution
posted on 01.02.2018 by Bhanudas Dattatray Mokar, Jinxian Liu, Rai-Shung Liu
This work describes three different strategies to structurally rearrange one 3-alkylidene-2H-1,2-oxazine molecule into three distinct heterocycles using HOTf, propiolic acid, and silica gel, respectively. The mechanisms of these rearrangement reactions involve three independent routes, including (i) Brønsted acid catalysis, (ii) a synergetic action of Brønsted acids and anions, (iii) a surface-directed chemoselectivity.