Chemiluminescent Autoxidation of a-Silyl Carbanions Derived from 9-Silyl-10-methylacridanes

The autoxidation of α-silyl carbanions derived from 9-trimethysilyland 9-triphenylsilyl-10-methylacridanes (la and 1b) produced the fluorescent N-methylacridone (NMA) accompanied by weak chemiluminescence. Differences in the chemiluminescence quantum yields and the time course of the light emission were detected between the reactions of la and 1b, which was due to the substituent on the silicon atom. Additionally, the 9-trimethylsilyl-10-methylacridinium salt also underwent a chemiluminescent reaction when reacted with alkaline hydrogen peroxide. It is probable that these chemiluminescent reactions would proceed via the Peterson-type reaction and involve the dioxasiletanide-like species during the reaction pathway.