2-naphthoyl azide

Comprehensive studies of the photochemistry of 2-naph-thoyl and substituted benzoyl azides were undertaken to determine the multiplicity of the ground state of aroylni-trenes. Irradiation (254 nm) of 2-naphthoyl azide (26) in cyclohexane at room temperature produces N-cyclo-hexyl-2-naphthamide (27, -45%), 2-naphthyl isocyanate (28, -50%), and a trace (<1%) of 2-naphthamide (29). 

Direct and triplet sensitized irradiation of 3-naphthoyl azide gave nitrene-derived products characteristic of reaction only from the singlet state. 

The suggestion" that )8-naphthoyl azide could be used as a reagent for the determination of amines could be used in reverse i.e. treatment of a suspected acid azide with a known amine should yield a urethane and molecular nitrogen according to equation (1). 

Acylated aromatic amino acids can often be degraded successfully. 2-Acetamido-3-naphthoyl hydrazide gives the azide, which rearranges to N-acetylnaphthimidazolone. ... 

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