Reactions of Phenols
Phenols react in a wide variety of ways.
- Esterfication reactions and ether formation
- Electrophilic aromatic substitutions as the hydroxyl group is activating, for example synthesis of calixarenes
- Reaction of naphtols and hydrazines and sodium bisulfite in the Bucherer carbazole synthesis
- Oxidative cleavage, for instance cleavage of 1,2-dihydroxybenzene to the monomethylester of 2,4 hexadienedioic acid with oxygen, copper chloride in pyridine
- Oxidative de-aromatization to quinones also known as the Teuber reaction. Oxidizing reagents are Fremy's salt and oxone. In reaction depicted below 3,4,5-trimethylphenol reacts with singlet oxygen generated from oxone/sodium carbonate in an acetonitrile/water mixture to a para-peroxyquinole. This hydroperoxide is reduced to the quinole with sodium thiosulfate.
- Phenols are oxidized to hydroquinones in the Elbs persulfate oxidation
- Phenolate anions (deriving from phenols by the loss of H+) can act as ligands towards metal cations.
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“Cuteness in children is totally an adult perspective. The children themselves are unaware that the quality exists, let alone its desirability, until the reactions of grownups inform them.”
—Leontine Young (20th century)
“Cuteness in children is totally an adult perspective. The children themselves are unaware that the quality exists, let alone its desirability, until the reactions of grownups inform them.”
—Leontine Young (20th century)