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Paper | Regular issue | Vol 29, No. 6, 1989, pp.1041-1064
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4762
Electron Transfer - Induced Photochemical Reactions in Imide- RXCH2 TMS Systems. Photoaddition of α-Trimethylsilyl Substituted Heteroatom Containing Compounds to Phthalimides

Ung-Chan Yoon,* Hyun-Jin Kim, and Patrick S. Mariano

*Department of Chemistry , College of Natural Sciences, Pusan National University, Kumjeong-ku, Pusan 609-735, Korea

Abstract

Studies have been conducted to explore single electron transfer (SET) induced photoaddition reactions of phthalimides with the α-silyl-n-electron donors (EtOCH2TMS, n-PrSCH2TMS and Et2NCH2TMS). Photoadditions of EtOCH TMS, n-PrSCH2TMS and Et2NCH2TMS to phthalimides in CH3CN or CH3OH occur in moderate to high yields to produce 3-substituted phthalimidines. The primary photoadducts undergo dehydration (or desilanolation) to generate 3-alkylidenylphthalimidine derivatives by pathways which are accelerated by acid impurity. Mechanisms for these photoadditions involving SET from α-silyl-n-electron donors to excited phthalimides followed by selective desilylation of the intermediate cation redicals and radical coupling are proposed.