Oxidation of isosafrole by sodium hypochlorite catalysed by manganese porphyrins: Unusual competition between epoxidation and O-dealkylation

Article abstract of DOI:10.1016/0040-4039(95)02312-7

Isosafrole (1a) and isoeugenol methyl ether (1b), two closely related substrates, behave very differently when subjected to manganese porphyrins catalysed epoxidation by sodium hypochlorite. A possible explanation is given, in terms of an unusual competition between the epoxidation and the O-dealkylation of the -OCH₂O-moiety.