A NEW TYPE OF INDUCED DECOMPOSITION. III. INDUCED DECOMPOSITION OF CINNAMOYL PEROXIDE, T-BUTYL PEROXYCINNAMATE AND T-BUTYL 2,3-DIPHENYLPEROXYPROPIONATE IN SOLUTION

Phenyl and benzyl radicals were found to induce decomposition of cinnamoyl peroxide or t-butylperoxycinnamate to give stilbene and 1,3-diphenylpropene, respectively. Similarly, t-butoxyl radicals caused t-butyl 2,3-diphenylperoxypropionate to decompose affording stilbene. A mechanism is proposed which involves a radical atttack on a substrate peroxide producing a radical carrying an odd electron on the carbon atom β to the carboxyl group and its subsequent collapse to final products by way of β-scission.