Grignard reagent-mediated conversion of an acyl nitroso-anthracene cycloadduct to a nitrone |
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Authors: | Chen Weibin Day Cynthia S King S Bruce |
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Institution: | Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA. |
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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. |
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