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Reduction of dixanthylidene with potassium or lithium resulted in formation of the antiaromatic dianion in high yield. Attempts to form the dianion by excited-state deprotonation of dixanthene with n-butyllithium/TMEDA resulted in formation of the tetraanion from deprotonation ortho to the oxygen. Orientation of the sp(3) hydrogens presumably allows preferential deprotonation of the xanthene rings.

Antiaromatic Dianions: Dianions of Dixanthylidene by Reduction and Attempted Excited-State Deprotonation