Homolytic Alkylation Of Chromones In Micellar Solution

Treatment of an aqueous solution of chromone, the detergent sodium dodecylbenzenesulfonate, silver nitrate and an alkanoic acid, with ammonium peroxydisulfate gives 2-R-chromone [R = i-C3H7 (47%), R = t-C4H9 (65%) and R = 1-adamantyl (78%)]. In addition 2-R-4-chromanone [R = i-C3H7 (40%), R = t-C4H9 (5%) and R-1-adamantyl (10%)] is formed. It is proposed that the reaction involves as intermediate the relatively stable 2-R-4-chromanon-3-yl radical and that the detergent has a micellar catalytic activity on the free radical alkylation process.