Practical Access to C-Unsubstituted 1,2-Diazetidines

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The Cui Group and collaborators have developed an operationally simple and direct synthesis of 1,2-disulfonyl-1,2-diazetidine derivatives, a unique class of highly strained N-heterocycles, via a one-step intermolecular dialkylation reaction. Structural features of these distinctive cyclic systems have been understood by experimental and computational Raman study. Among three different types of bonds in the ring skeleton, selective N‒N bond cleavage of the resulting 1,2-diazetidines was shown and enabled a new pathway for a stereoselective access to C-aminomethyl-N‑sulfenylimines.

Chaminda Lakmal, H. H.; Xu, J. X.; Xu, X.; Ahmed, B.; Fong, C.; Szalda, J. D.; Ramig, K.; Sygula, A.; Webster, C. E.; Zhang, D.; Cui X. “Synthesis of C-Unsubstituted 1,2-Diazetidines and Their Ring-Opening Reactions via Selective N–N Bond Cleavage” J. Org. Chem. 2018, 83, 9497. (doi)

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