Unexpected Squaramide-Induced Cleavage of Benzils: Synthesis and Characterization of Mono-Aroyl Squarimides

We report the reaction of 4,4′-substituted benzils with squaramides (SQ) affording mono-squarimides (SQIs). The 1H NMR and X-ray structures of the SQIs (R = H) revealed the existence of a strong C=O···HN intramolecular hydrogen-bond motif. The unprecedented reaction between SQs and benzils highlights the difference in reactivity between urea and squaramide units.

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E. Sanna, C. López, P. Ballester, C. Rotger, A. Costa

Eur. J. Org. Chem. 2015, 7656-7660
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