A new methodology for the bis(oxyocyclohexadienyl) peroxide fromation

摘要

Symmetrically substitute bis(4-oxocyclohexa-2,5-dienyl) peroxide 5 (R=R) as well as unsym- metrically substituted 5 (R≠R') can be prepared efficiently by treating 4-halogenocyclohexa-2,5- dienone 3 with 4-hydroperoxycyclohexa-2,5-dienone 4 in the presence of an appropriate positive halogen compound such as N-iodosuccinimide. Acetonitrile is a suitable solvent for the reactions. The formation of 5 is suggested to take place via electrophilic attack by the positive halogen species Upon 3 generating the 4-oxocyclohexa-2,5-dienyl cation (or the phenoxy cation), followed by Numcleophilic attack by 4 upon the cation.