Benzophenone imine
Benzophenone imine is an organic compound with the formula of 2C=NH. A pale yellow liquid, benzophenone imine is used as a reagent in organic synthesis.
Synthesis
Benzophenone imine can be prepared by the thermal decomposition of benzophenone oxime:Benzophenone imine can also be synthesized by addition of phenylmagnesium bromide to benzonitrile followed by careful hydrolysis :
This method is known as Moureu-Mignonac ketimine synthesis.
Yet another route to benzophenone imine involves reaction of benzophenone and ammonia.
Reactions
Benzophenone imine undergoes deprotonation with alkyl lithium reagents.Primary amines can be protected as benzophenone imines, and the protected amines are stable in flash chromatography.
Buchwald-Hartwig amination involves coupling aromatic halide and amine to form carbon-nitrogen bonds with the help of palladium-based catalysts. Benzophenone imine can be used as an ammonia-equivalent in such reactions.