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Improved Xanthone Synthesis, Stepwise Chemical Redox Cycling.

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A base-catalyzed direct oxidation of rhodamine, carborhodamine, and siliconrhodamine pyronines to the corresponding xanthones is studied. This methodology utilizes addition of water to split pyronines into xanthone and reduced xanthene,… Click to show full abstract

A base-catalyzed direct oxidation of rhodamine, carborhodamine, and siliconrhodamine pyronines to the corresponding xanthones is studied. This methodology utilizes addition of water to split pyronines into xanthone and reduced xanthene, the latter of which is returned to pyronine by oxidation with iodine. The transformation is general, working on the three most recalcitrant versions of N, N, N', N'-tetramethylpyronines in good to excellent yields.

Keywords: redox cycling; xanthone synthesis; stepwise chemical; synthesis stepwise; chemical redox; improved xanthone

Journal Title: Organic letters
Year Published: 2019

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