The exposure of 2,4,6-tri-tert-butylphenol (1) in solution to NO 2 · results in the rapid formation of 2,4,6-tri-tert-butyl-4-nitro-2,5-cyclohexadienone (2), which then undergoes a slow (ca. 3 d) rearrangement in the absence of air. The mechanism that describes this rearrangement is understood for the first time and involves the initial isomerization of 2 to form a (-ONO)-substituted cyclohexadieneone (6). The nitrite moiety undergoes bond homolysis releasing NO · while forming
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