Abstract
Abstractα‐Phenyl‐4‐nitrobenzenemethanol (3) reacted with 1 M sodium hydroxide to yield 4, 4′‐dibenzoyl‐azoybenzene (5) (51%), 4‐hydroxy‐4′‐benzoylazobenzene (6) and benzoic acid (12% each), and smaller amounts of 4‐aminobenzophenone and 4‐nitrobenzophenone. Both α‐phenyl‐2‐nitrobenzenemethanol (9) and 3, 5‐dimethyl‐4‐nitrobenzenemethanol (10a) did not react with 1 M sodium hydroxide, presumably due to steric hindrance. α‐(p‐Nitrophenyl)‐4‐pyridinemethanol (14) and its N‐oxide 11 with 1 M sodium hydroxide yielded 4,4′‐diaroylazoxybenzenes 15a and 12a, respectively, 4,4′‐diaroylazobenzenes 15b and 12b, respectively, as well as 4‐hydroxy‐4′‐aroylazobenzenes 16 and 13, respectively. The relative reaction rates were 11 > 14 > 3. Studies with 11 showed that the nitro group is involved in the redox reaction in preference to the N‐oxide group.
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