CCV.—Colour and constitution of azo-compounds. Part VI

Hewitt, John Theodore; Mann, Gladys Ruby; Pope, Frank George

doi:10.1039/ct9140502193

J. Chem. Soc., Trans.

1914

DOI: 10.1039/ct9140502193

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CCV.—Colour and constitution of azo-compounds. Part VI

John Theodore Hewitt¹,

Gladys Ruby Mann²,

Frank George Pope³

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1996

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Hydroxide‐promoted redox reactions in water of α‐Phenyl‐4‐nitro‐benzenemethanol, α‐(p‐Nitrophenyl)‐4‐pyridinemethanol, and α‐(p‐Nitrophenyl)‐4‐Pyridinemethanol N‐Oxide steric inhibition of resonance

Muth

Yang

1996

Journal of Heterocyclic Chem

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α‐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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Hydroxide‐promoted redox reactions in water of α‐Phenyl‐4‐nitro‐benzenemethanol, α‐(p‐Nitrophenyl)‐4‐pyridinemethanol, and α‐(p‐Nitrophenyl)‐4‐Pyridinemethanol N‐Oxide steric inhibition of resonance

Muth

Yang

1996

Journal of Heterocyclic Chem

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4-Hydroxy-4?-ethynylazobenzene

1965

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CCV.—Colour and constitution of azo-compounds. Part VI

Cited by 2 publications

References 0 publications

Hydroxide‐promoted redox reactions in water of α‐Phenyl‐4‐nitro‐benzenemethanol, α‐(p‐Nitrophenyl)‐4‐pyridinemethanol, and α‐(p‐Nitrophenyl)‐4‐Pyridinemethanol N‐Oxide steric inhibition of resonance

Hydroxide‐promoted redox reactions in water of α‐Phenyl‐4‐nitro‐benzenemethanol, α‐(p‐Nitrophenyl)‐4‐pyridinemethanol, and α‐(p‐Nitrophenyl)‐4‐Pyridinemethanol N‐Oxide steric inhibition of resonance

4-Hydroxy-4?-ethynylazobenzene

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