Abstract
Free Radical Reactions of N-Heterocyclic Compounds. XI. Reaction of 3-Methyl-pyrazolin-5-ones with Phenoxy Radicals Pyrazolin-5-ones (3a–i) were oxidized with 2,4,6-trisubstituted phenoxy radicals (2a–d) to the corresponding radicals (4a–i), which dimerised or combined with phenoxy radical (2a) depending on the R1- and R4-substituents in (3). In the case of 3-methyl-1-phenyl-pyrazolin-5-one (3f) the primary radical combination products were not found, but the corresponding quinone methide (17) and the o-phenol derivative (18) were isolated. Products and yields have been investigated as a function of mol ratio substrate: oxidant and solvent. The radical combination products (7–10) could de-tertbutylated in the presence of aluminium chloride or in the presence of trifluoroarcetic acid, forming heterocyclic substituted phenols (21) and (22).
Published Version
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