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Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
3-(2-Acetamido-phen-yl)sydnone
David A Grossie1, Kenneth Turnbull, Sandra Felix-Balderrama
1Department of Chemistry, Wright State University, 3640 Colonel Glenn Hwy, Dayton, Ohio 45435, USA.
Abstract:
Sydnones are unusual mesoionic compounds containing a five-membered heterocyclic ring. Generally for stability, substitution at the N-3 position by an aromatic fragment is necessary. In the title compound, C(10)H(9)N(3)O(3), the aromatic substitutent is 2-acetamido-phenyl. The two planar ring fragments are twisted relative to one another, with a inter-planar angle of 63.13 (5)°. The mol-ecules are packed into the unit cell via π-π inter-actions between the phenyl rings [inter-planar separation = 3.4182 (4) Å] and between the sydnone rings [inter-planar separation = 3.2095 (4) Å]. N-H⋯O and C-H⋯O hydrogen bonding is also found inter-nally and externally to the mol-ecule.
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