ChemInform Abstract: Photochemical Ring Expansion of α‐Alkoxycyclobutanones to 2‐Acetoxy‐5‐alkoxytetrahydrofurans: Nucleophilic Reactions at the 2‐Position.

Abstract

Photochemical Ring Expansion of α-Alkoxycyclobutanones to 2-Acetoxy-5-alkoxytetrahydrofurans: Nucleophilic Reactions at the 2-Position.-Irradiation of cyclobutanones in the presence of nucleophiles results in efficient ring expansion to tetrahydrofurans, with retention of configuration of all resident stereocenters, but with no stereoselectivity at the newly formed stereogenic center. The tetrahydrofurans smoothly undergo substitution with a variety of nucleophiles at the 2-position. -(UMBRICHT, G.; HELLMAN, M. D.; HEGEDUS, L. S.; J. Org. Chem. 63 (1998) 15, 5173-5178; Dep. Chem., Colo. State Univ., Fort Collins, CO 80523, USA; EN)