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A Masked 1,3-Dipole Revealed from Aziridines


  • We wish to thank the Institut de Chimie des Substances Naturelles for financial support and a fellowship.


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Double agent: Switching the electronic nature of substituents on an aziridine ring induces the formation of the ring-opened zwitterionic 1,3-dipole through C[BOND]N bond cleavage instead of the usual C[BOND]C 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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