CHROMIUM(VI) OXIDE-CATALYZED OXIDATION OF AROMATIC OLEFINS BY TERT-BUTYL HYDROPEROXIDE

(E)- and (Z)-stilbenes, styrene and norbornene have been subjected to oxidation by catalytic amounts of CrO3 and an excess of aqueous 70% t- BuOOH. Norbornene was unreactive; (E)-stilbene was more reactive than the (Z)-isomer. Both (E)- and (2)-stilbenes afforded mainly trans-stil bene oxide, benzil, benzoin benzoate and benzophenone; styrene led to styrene oxide, 1,2-di-(t-butylperoxy)-phenylethane, benzaldehyde and b enzoic acid. A mechanism involving a benzylic radical coordinated to c hromium through a peroxy bond as intermediate is proposed to rationali ze the results.