Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 24, Pages 9221-9224Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0615192
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Funding
- NHLBI NIH HHS [R01 HL062198, HL 62198] Funding Source: Medline
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[GRAPHICS] 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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