Journal of Photosciences
Photoaddition Reactions of N-Methylthiophthalimide with a-Silyl-nelectron Donors via Single Electron Transfer-Desilylation and Hydrogen Atom Abstraction Pathways
Volume 9(2002), 17-22 page
ÀúÀÚ: Ung Chan Yoon, Sun Wha Oh, Seong Chul Moon and Tae Gyung Hyung
9-1-17.pdf (123.3K)
Keywords:
photoaddition reaction N-methylthiophthalimide a-silyl-n-electron donors single electron transfer hydrogen atom abstraction
Studies have been conducted to explore photoaddition reactions of N-methylthiophthalimide with a-silyl-nelectron donors Et2NCH2SiMe3 , n-PrSCH2SiMe3 and EtOCH2SiMe3.
Photoaddition of a-silyl amine Et2NCH2SiMe3 to N-methylthiophthalimide occurs in CH3CN and benzene to produce non-silicon containing adduct in which thiophthalimide thione carbon is bonded to a-carbon of a-silyl amine in place of the trimethylsilyl group.
In contrast, photoaddition of EtOCH2SiMe3 to N-methylthiophthalimide generates two diastereomeric adducts in which thiophthalimide thione carbon is connected to a-carbon of a-silyl ether in place of a-hydrogen.
Based on a consideration of the oxidation potentials of a-silyl-n-electron donors and the nature of photoadducts, mechanism for these photoadditions involving single electron transfer (SET) -desilylation and H atom abstraction pathways are proposed.
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