Reactivity of tetrapyrrolyl nitrones towards dipolarophiles bearing electron-withdrawing groups

Abstract

The reactivity of porphyrinyl and corrolyl nitrones towards dipolarophiles bearing electron-withdrawing groups was studied and it was found that the two nitrones behave differently in 1,3-dipolar cycloaddition reactions. While porphyrinyl nitrone reacts with dimethyl fumarate, dimethyl acetylenedicarboxylate and ethyl propiolate to afford the expected isoxazolidine and isoxazoline cycloadducts, the corrolyl nitrone reacts with dimethyl fumarate to provide an isoxazolidine-substituted corrole but with dimethyl acetylenedicarboxylate it gives amide derivatives. (C) 2015 Elsevier Ltd. All rights reserved.