70702-91-9Relevant academic research and scientific papers
The slow rearrangement of a sterically hindered nitro-cyclohexadienone and the absence of phenol oxidation by nitrogen monoxide
Peters, Steven J.,Blood, Trisha M.,Kassabaum, Mark E.
, p. 6104 - 6108 (2009)
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-4nitro-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 an oxyl radical intermediate. An lntermolecular, concerted hydrogen abstraction, which proceeds between 6 and this oxyl radical, results in the simultaneous formation of all stable products, some of which have not been previously observed, Furthermore, when 1 is exposed, to NO. under anaerobic conditions, no reaction is observed. Wiley-VCH Verlag GmbH & Co. KGaA.
