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Note | Regular issue | Vol 63, No. 7, 2004, pp.1667-1672
Published online, 1st June, 2004
DOI: 10.3987/COM-04-10094
Chemiluminescent Autoxidation of α-Silyl Carbanions Derived from 9-Silyl-10-methylacridanes

Jiro Motoyoshiya,* Kunihiko Tokutake, Motoki Kuroe, Sachiko Yoshioka, Yoshinori Nishii, and Hiromu Aoyama

*Department of Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan

Abstract

The autoxidation of α-silyl carbanions derived from 9-trimethysilyl- and 9-triphenylsilyl-10-methylacridanes (1a 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 1a 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.