Graham reaction

In organic chemistry, the Graham reaction is an oxidation reaction that converts an amidine into a diazirine using a hypohalite reagent. The halide of the hypohalite oxidant, or another similar anionic additive to the reaction, is retained as a substituent on the diazirine product. The reaction was first reported in 1965. Various reaction mechanisms have been proposed.


 * Graham-reaction-2D-scheme.svg

Amidine substrates for the reaction can easily be formed from the corresponding nitriles via the Pinner reaction. The halide substituent in the diazirine product can be displaced by a various nucleophiles.


 * [[File:Diazirine Exchange screenshot.png]]