We are studying the solution-phase rearrangements and cyclizations of arenes catalyzed by superacids at temperatures from ambient to ca. 200 �C. Under these conditions, aryl groups migrate freely and complex skeletal rearrangements can be observed. We find that anthracene rearranges to phenanthrene. DFT computations support an aryl pirouette mechanism. Efforts to prepare five-membered rings from diarylmethanes and the exploration of a wider assortment of superacid-catalyzed arene rearrangements will be described. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/242nm/uploads/84100_image1.jpg' alt='' />

High temperature cationic rearrangements of arenes

245th National Meeting (2013)

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