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A Simple Method for the Synthesis of Substituted Benzylic Ketones: Homologation of Aldehydes via the in Situ Generation of Aryldiazomethanes from Aromatic Aldehydes

Steven R. Angle and Martin L. Neitzel

*Department of Chemistry, University of California-Riverside, Riverside, California 92521-0403, Email:

S. R. Angle, M. L. Neitzel, J. Org. Chem., 2000, 65, 6458-6461.

DOI: 10.1021/jo000446y

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Aryldiazomethanes can be generated in situ by simply heating the tosylhydrazones of aromatic aldehydes in the presence of a stoichiometric amount of base in polar protic solvents. In the presence of aldehydes, benzylic ketones are formed in good yields. In addition, tosylhydrazones can be prepared in ethanol and carried through the sequence without isolation.

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Key Words

ketones, benzylations

ID: J42-Y2000