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Oxidative cleavage of benzylic and related ethers, using an oxoammonium salt

Oxidative cleavage of benzylic and related ethers, using an oxoammonium salt

Journal of Organic Chemistry 74(24): 9524-9527

Benzylic ethers and related ArCH(2)OR substrates are oxidatively cleaved by 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in wet CH(3)CN at room temperature to give the corresponding aromatic aldehyde and alcohol in high yield. Primary or secondary alcohol products are further oxidized by 1 to give carboxylic acids and ketones, respectively. The oxidation likely involves a formal hydride abstraction from the benzylic carbon as evidenced by slow reaction of substrates bearing electron-withdrawing substituents.

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Accession: 054825662

Download citation: RISBibTeXText

PMID: 19877704

DOI: 10.1021/jo902144b

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