Returning back to the drawing board, we considered the smallest functional group possible analogous to the diazirines enlisted for photoaffinity labeling. The insertion of a single carbonyl group into a diazirine with the reduction of N=N double bond led to the proposal of the diazetidinone (DZE) 10 (Figure ). This small, strained ring system was designed based on the intuitive notion that the embedded hydrazine motif would be readily oxidized to release a ketene upon nitrogen extrusion. Indeed, it is predicted that thermolysis of analogous structure could lead to ketene formation by cycloreversion, further supporting the notion that DZEs are prone to fragment into ketenes upon suitable activation. Of note, DZEs are a rarely utilized functional group in organic synthesis. Their main use is as a bioisostere of β-lactams, and acylated variants have been identified as serine-selective probes. Many methods for their preparation have been reported, yet their value as intermediates in synthesis is underexplored, and the electrochemical