Chemiluminescent autoxidation of alpha-silyl carbanions derived from 9-silyl-10-methylacridanes

摘要

The autoxidation of alpha-silyl carbanions derived from 9-trimethysilyl-and 9-triphenylsilyl-10-methylacridanes (la and Ib) 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 Ib,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.