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A simple method for the α-oxygenation of aldehydes

Beshara, Cory S. and Hall, Adrian and Jenkins, Robert L. and Jones, Teyrnon C. and Parry, Rachael T. and Thomas, Stephen P. and Tomkinson, Nicholas C. O. (2005) A simple method for the α-oxygenation of aldehydes. Chemical Communications (11). pp. 1478-1480. ISSN 1359-7345

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A mild, efficient and general method for the chemospecific α-oxygenation of aldehydes is described. Treatment of a series of aldehydes with N-tert-butyl-O-benzoyl hydroxylamine hydrochloride gives the corresponding α-oxygenated carbonyl via a proposed pericyclic rearrangement process.