Phenyl azide
Phenyl azide is an organic compound with the formula C6H5N3. It is one of the prototypical organic azides. It is a pale yellow oily liquid with a pungent odor. The structure consists of a linear azide substituent bound to a phenyl group. The C−N=N angle is approximately 116°. It was discovered in 1864 by Peter Griess by the reaction of ammonia and phenyldiazonium.
Preparation
Phenyl azide is prepared by the diazotization of phenylhydrazine with nitrous acid:Aryl iodides bearing electron-withdrawing substituents undergo metathesis with sodium azide in the presence of Cu, sodium ascorbate, and N,N'-dimethylethane-1,2-diamine :
It can also be prepared by condensation of benzenediazonium salt with toluenesulfonamide, followed by hydrolysis.
Chemical reactions
Phenyl azide cycloadds to alkenes and especially Azide alkyne [Huisgen cycloaddition|alkynes], particularly those bearing electronegative substituents. In a classic example of click chemistry, phenyl azide and phenylacetylene react to give diphenyl triazole.Phenyl azide reacts with triphenylphosphine to give the Staudinger reagent triphenylphosphine phenylimide.
Thermolysis induces loss of N2 to give the highly reactive phenylnitrene C6H5N.