Dearomatization Reactions Using Phthaloyl Peroxide

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• 作者：Anders M. Eliasen ; Mitchell Christy ; Karin R. Claussen ; Ronald Besandre ; Randal P. Thedford ; Dionicio Siegel
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：September 18, 2015
• 年：2015
• 卷：17
• 期：18
• 页码：4420-4423
• 全文大小：327K
• ISSN：1523-7052

文摘

A new oxidative dearomatization reaction has been developed using phthaloyl peroxide to chemoselectively install two oxygen鈥揷arbon bonds into aromatic precursors. The oxidation reaction proceeds only once; addition of superstoichiometric equivalents of phthaloyl peroxide does not react further with the newly generated 1,3-cyclohexadiene. The reaction has been challenged by the addition of different functional groups and shown to maintain chemoselectivity. Due to the broad reactivity with 1,2-methylenedioxybenzene derivatives, linear free energy correlations were determined and support a mechanism proceeding through diradicals analogous to arene-hydroxylation reactions using phthaloyl peroxide.