The reactivity of polyhydric phenols towards air and m-chloroperbenzoic acid. The nature of the monomeric products
The products of a series of polysubstituted phenols, previously shown to exhibit increasing reactivity towards oxygen, were characterised when air and m-chloroperbenzoic acid were used separately as oxidants.
The latter reagent gave compounds derived from oxidation of the unsaturated side-chains and, for the more reactive phenols, products derived by oxidation at the aromatic nucleus. In the case of air, only the more reactive phenols gave products, and these were mainly derived by oxidation at the aromatic nucleus. In particular 2,4-di-isopentenylphloroglucinol gave 3,4-dihydroxy-2,4-di-isopentenylcyclohexa-1,5-dione which was isomerised in sodium carbonate to 3,4-dihydroxy-2-isopentenyl-4-isohexenoylcyclopent-2-enone. 2,4,6-Tri-isopentenyl-phloroglucinol gave 3,4-dihydroxy-2,4,6-tri-isopentenylcyclohex-2-en-1,5-dione which, on prolonged exposure to air, afforded 3,5-dihydroxy-2.5-di-isopentenylcyclopent-2-ene-1,4-dione.