Tetrahedron Letters

A bifunctional approach towards the mild oxidation of organic halides: 2-dimethylamino-N, N-dimethylaniline N-oxide

S Chandrasekhar, M Sridhar

Index: Chandrasekhar, Sosale; Sridhar, Malayalam Tetrahedron Letters, 2000 , vol. 41, # 28 p. 5423 - 5425

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Citation Number: 34

Abstract

The titled reagent incorporates an oxygen-centred nucleophile and a basic moiety—in a suitably mutual orientation—in the same molecule. It oxidises various primary benzylic bromides to the corresponding aromatic aldehydes under relatively mild conditions (MeCN/rt– 50° C/6–24 h) in high yields (83–97%), and is thus a useful alternative to the Kornblum procedure.

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