title: Grignard reagent-mediated conversion of an acyl nitroso-anthracene cycloadduct to a nitrone.
abstract: An intramolecular hetero-Diels-Alder cycloadduct of an acyl nitroso compound and a 9,10-dimethyl anthracene derivative was prepared as a potential nitroxyl (HNO) donor. This compound did not release HNO under any of the conditions tested. Treatment of this cycloadduct with excess MeMgCl resulted in the formation of a nitrone, whose structure was confirmed by X-ray crystallography. A mechanism where MeMgCl acts as a nucleophile, strong base, and Lewis acid possibly explains the formation of this product.
authors.affiliation: Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
authors.forename: Weibin
authors.initials: W
authors.lastname: Chen
authors.forename: Cynthia S
authors.initials: CS
authors.lastname: Day
authors.forename: S Bruce
authors.initials: SB
authors.lastname: King
mesh_terms: D000873:Anthracenes / Q000737:chemistry*; D003500:Cyclization; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009603:Nitroso Compounds / Q000737:chemistry*
chemical_list: D000873:Anthracenes; D007202:Indicators and Reagents; D009603:Nitroso Compounds; C034020:anthracene