Journal of Organic Chemistry p. 1422 - 1428 (1992)
Update date:2022-08-02
Topics:
Yoon, Ung Chan
Kim, Yong Chul
Choi, Jeong Ja
Kim, Dong Uk
Mariano, Patrick S.
et al.
Studies have been conducted to explore single electron transfer (SET) induced photoaddition reactions of acenaphthylenedione (ACND) with the n-electron donors Et2NCH2SiMe3, n-PrSCH2SiMe3, EtOCH2SiMe3, EtCO2CH2N(CH2Ph)CH2SiMe3, and EtCO2CH2N(CH2Ph)CH3.Photoaddition of α-silyl amine Et2NCH2SiMe3 to ACND occurs in CH3OH and CH3CN to produce 2-hydroxy-2-<(diethylamino)methyl>acenaphthylen-1-one.In contrast, photoaddition of n-PrSCH2SiMe3 to ACND generates two photoadducts, 2-hydroxy-2-<(n-propylthio)methyl>acenaphthylen-1-one and 2-hydroxy-2-<(n-propylthio)(trimethylsilyl)methyl>acenaphthylen-1-one, along with a ACND photoreduction dimer.Photoaddition of EtOCH2SiMe3 to ACND produces two diastereomers of 2-hydroxy-2-
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