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Photochemical Ring Expansion of α-Alkoxycyclobutanones to 2-Acetoxy-5-alkoxytetrahydrofurans:  Nucleophilic Reactions at the 2-Position

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posted on 25.06.1998, 00:00 by Gisela Umbricht, Melissa D. Hellman, Louis S. Hegedus
Photolysis of cyclobutanones in the presence of acetic acid produced 2-acetoxy-5-alkoxytetrahydrofurans regiospecifically and with retention of configuration at the migrating α-position. The acetoxy group was replaced by nucleophiles such as allylsilane, trimethylsilyl azide, diethylaluminum cyanide, and silylated thymine in the presence of Lewis acids.

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