Abstract
AbstractA facile synthesis of 2, 5‐diamino‐p‐benzoquinones (DABQs) is reported under very mild conditions by mere crystallization. Mechanistic studies by density functional theoretical (DFT) calculations revealed an oxidative C(sp2)‐C(sp2) bond cleavage reaction mechanism via a dioxetane intermediate, from enamine oxidation of a mixture of ethyl vanillin and primary amines by triplet molecular oxygen. A second air oxidation event in the sequence of the reaction that results in C(sp2)‐C(sp2) bond formation is also described by DFT studies. The mechanistic insights enabled synthesis of both symmetric and unsymmetric DABQs from primary amines with a broad substrate scope.
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