Nitrone cycloaddition to quinones: A novel strategy for the synthesis of benzisoxazolidenes

Abstract

1,3‐Dipolar cycloaddition reaction involving nitrones and benzoquinones resulting in the formation of benzisoxazolidene is described. As the nitrone is selectively added to carbon–carbon double bond of the benzoquinone, the quinone‐nitrone reaction is considered as a special case among quinone‐1,3‐dipole cycloaddition reactions. Molecular orbital calculation was performed to examine the electronic effects involved in the regioselectivity of the reaction. J. Heterocyclic Chem., (2010).