| 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 ). |
