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.^[1] Various reaction mechanisms have been proposed.^[2][3]

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.^[4]