Triphenylphosphine/NBS-Catalyzed Beckmann Rearrangement of Ketoximes into Amides
A Beckmann rearrangement of ketoximes reaction using triphenylphosphine/NBS as an effective catalyst in acetonitrile is developed.The results indicate that conversion of oximes to amides can reach excellent yields(76％-99％yield)under mild reaction conditions.There are many merits about this method,such as low corrosion,high yields,large-scale preparation,environmental friendliness,simple work-up procedure,and short reaction time.The reaction mechanism is also proposed.The absorption and emission spectrum characteristics of the compounds are also examined.The N-phenyl-[1,1'-biphenyl]-4-carboxamide and 4-nitro-N-phenylbenzamide have a large Stokes shifts of 118,151 nm,respectively.The results indicate that altering the substitution of aromatic group can be an effective means to regulate the Stoke's shift.
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