Double agent: Switching the electronic nature of substituents on an aziridine ring induces the formation of the ring-opened zwitterionic 1,3-dipole through CN bond cleavage instead of the usual CC bond cleavage. This novel dipole reacts with alkenes, alkynes, nitriles, and carbonyl compounds to afford new types of [3+2] cycloadducts, thereby enhancing the diversity of nitrogen-containing heterocycles accessible through 1,3-dipolar cycloadditions. EWG=electron-withdrawing group.
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Dauban et al. (2009) studied this question.
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