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Updated: May 19, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Ring splitting of azetidin-2-ones via radical anions
Raúl Pérez-Ruiz1, Jose A Sáez, Luis R Domingo
1Departamento de Química/Instituto de Tecnología Química UPV-CSIC, Universitat Politécnica de València, Camino de Vera s/n, 46022, Valencia, Spain.
Abstract:
The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. The preference for β-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.
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