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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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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… Click to show full abstract

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.

Keywords: one alkylidene; nsted acids; alkylidene oxazine; oxazine molecule

Journal Title: Organic letters
Year Published: 2018

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