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Unexpected Squaramide‐Induced Cleavage of Benzils: Synthesis and Characterization of Mono‐Aroyl Squarimides
Author(s) -
Sanna Elena,
López Carlos,
Ballester Pablo,
Rotger Carmen,
Costa Antoni
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501235
Subject(s) - squaramide , chemistry , intramolecular force , cleavage (geology) , reactivity (psychology) , hydrogen bond , medicinal chemistry , stereochemistry , organic chemistry , catalysis , molecule , organocatalysis , enantioselective synthesis , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering
Abstract We report the reaction of 4,4′‐substituted benzils with squaramides (SQ) affording mono‐squarimides (SQIs). The 1 H 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.