Add time:08/02/2019 Source:sciencedirect.com
N,N-dimethylhydrazones of aldehydes can be efficiently oxidized in a catalytic way by hydrogen peroxide associated with methyltrioxorhenium (MTO) as the catalyst to give nitriles. Elimination of dimethylhydroxylamine that is further oxidized to N-methyl-N-methylene N-oxide takes place. This nitrone was fully characterized as such and also as its cycloaddition product with methylmethacrylate. This system tolerates many other functionalities and especially carbon–carbon double bonds which are not epoxidized under the precise conditions outlined herewith. The reaction has also been extended to a few hydrazones derived from ketones: a good recovery of the ketones is again observed. In one case, the fate of the protecting group could also be established: as for hydrazones of aldehydes, a nitrone is formed upon the nitrogen–nitrogen bond rupture.
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