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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.

SUBMITTER: Chen W

PROVIDER: S-EPMC3481167 | biostudies-literature | 2006 Nov

REPOSITORIES: biostudies-literature

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Grignard reagent-mediated conversion of an acyl nitroso-anthracene cycloadduct to a nitrone.

Chen Weibin W Day Cynthia S CS King S Bruce SB

The Journal of organic chemistry 20061101 24

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 ...[more]

PMID: 17109552

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