Dearomatization Reactions Using Phthaloyl Peroxide

• DOI: 10.1021/acs.orglett.5b02008
• Publication Date: 2015-09-01T14:24:57Z
• Authors: Anders M. Eliasen; Mitchell Christy; Karin R. Claussen; Ronald Besandre; Randal P. Thedford; Dionicio Siegel
• Keywords: Peroxide; Chemoselectivity; Hydroxylation; Reactivity

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