HYDROXIDE-PROMOTED REDOX REACTIONS IN WATER OF ALPHA-PHENYL-4-NITROBENZENEMETHANOL, ALPHA-(P-NITROPHENYL)-4-PYRIDINEMETHANOL, AND ALPHA-(P-NITROPHENYL)-4-PYRIDINEMETHANOL N-OXIDE STERIC INHIBITION OF RESONANCE

摘要

alpha-Phenyl-4-nitrobenzenemethanol (3) reacted with 1 M sodium hydroxide to yield 4,4'-dibenzoylazoybenzene (5) (51%), 4-hydroxy-4'-benzoylazobenzene (6) and benzoic acid (12% each), and smaller amounts of 4-aminobenzophenone and 4-nitrobenzophenone Both alpha-phenyl-2-nitrobenzenemethanol (9) and 3,5-dimethyl-4-nitrobenzenemethanol (10a) did not react with 1 M sodium hydroxide, presumably due to steric hindrance. alpha-(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. [References: 18]