Mechanistic studies of the azomethine ylide-forming photoreactions of N-(silylmethyl) phthalimides and N-phthaloylglycine

Y Takahashi, T Miyashi, UC Yoon, SW Oh…

Index: Takahashi, Yasutake; Miyashi, Tsutomu; Yoon, Ung Chan; Oh, Sun Wha; Mancheno, Maria; Su, Zhuoyi; Falvey, Daniel F.; Mariano, Patrick S. Journal of the American Chemical Society, 1999 , vol. 121, # 16 p. 3926 - 3932

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Citation Number: 37

Abstract

In earlier studies we have shown that irradiation of MeCN solutions of N-[(trimethylsilyl) methyl] phthalimide and N-phthaloylglycine in the presence of electron-defecient olefins (eg, methyl acrylate) results in the production of cycloadducts. In addition, irradiation of these substances in aqueous MeCN leads to formation of N-methylphthalimide. Laser flash photolysis and fluorescence spectroscopy have now been employed to investigate the ...