Grignard reagent-mediated conversion of an acyl nitroso-anthracene cycloadduct to a nitrone.
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.
Chen
Weibin
W
Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
Day
Cynthia S
CS
King
S Bruce
SB
D000873:Anthracenes / Q000737:chemistry*; D003500:Cyclization; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009603:Nitroso Compounds / Q000737:chemistry*
D000873:Anthracenes; D007202:Indicators and Reagents; D009603:Nitroso Compounds; C034020:anthracene