Unexpected Squaramide‐Induced Cleavage of Benzils: Synthesis and Characterization of Mono‐Aroyl Squarimides | Zendy

Sanna Elena | Zendy; López Carlos | Zendy; Ballester Pablo | Zendy; Rotger Carmen | Zendy; Costa Antoni | Zendy

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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

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.

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