Aromatic Carbonyl Compounds from 2-Aryloxycarboxylic Acid Esters

Article abstract of DOI:10.1007/BF00809192

Reactions of 2-(4-methoxyphenoxy)propanoic acid methylester, aryloxyacetic acids and their derivatives with di-tert-butylperoxide at 150 deg C result in the formation of 4-methoxyacetophenone and benzaldehydes.This transformation is explained by a 1,2 O->C aryl-migration, induced by a capto-dativ substituted radical and followed by a β-fragmentation of an alkoxyradical.The success of this radical rearrangement depends heavily on the nature of the capto-substituent and on the reaction temperature.Both parameters are subjects of this investigation. - Keywords: Capto- dativ substituted radical; 1,2 O->C Arylmigration; Neophyllike radical rearrangement; S_H2-Reaction