Oxidative Cleavage of Benzylic and Related Ethers, Using an Oxoammonium Salt

Priya P. Pradhan, James M. Bobbitt* and William F. Bailey*

*Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, Email: james.bobbittuconn.edu, william.baileyuconn.edu

P. P. Pradhan, J. M. Bobbitt, W. F. Bailey, J. Org. Chem., 2009, 74, 9501-9504.

DOI: 10.1021/jo902144b

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Abstract

Benzylic ethers are oxidatively cleaved by 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in wet MeCN at room temperature to give the corresponding aromatic aldehydes and alcohols in high yield. Primary and secondary alkyl alcohols are further oxidized to give carboxylic acids and ketones, respectively.

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Key Words

Aldehydes, Ketones, Benzylic Ethers, TEMPO Derivatives

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ID: J42-Y2009-3670