Phenacyl Azide

Acetophenone, Azido Derivatives,C H,NsO, mw 161.16, N26.07%. Two isomers are described in the literature a -Azidoaceto-phenone, Triazoacetophenone, Phenacyl Azide, Benzoylazidomethane, N3-CHa CO" CeHs plates (from eth + petr eth), mp 17°. Reacts very explosively with coned sulfuric acid. Was prepd by prolonged shaking of m-bromoacetophenone with Na azide inaq ale, with cooling... 

D. Straw, JACS 75, 1642 2684-5(1953). fJiazotization of this comp and treatment, with NaNOa in dil acid gave expl o- azido-phenacyl azide... 

Pentryl. See 2-(2, 4, 6-Trinitro-N-nitranilino Ethanol Nitrate under Anilinoethanol and Derivatives A425-L to A429-R Pentryl Homologs A429-R Peracetic Acid, Benzylester. See.Acetyl-benzylperoxide A55-L Phenacyl Azide. See a>-Azidoacetophenone under Acetophenone A47-R Phenazone. See Antipyrine A471-R Phenetidine. See Aminophenetole A240-R Phenyl Abietate. See under Abietic Acid A4-L... 

Phenacyl bromide Aq. methanol-acetic acid Phenacyl azide 93 99, 101... 

Imidazoles have been obtained by pyrolysis of phenacyl azides, probably by dimerization of the intermediate imines. 2-Benzoyl-4(5)phenylmidazole (184) was obtained fix>m phenacyl azide in 64% yield A more general method, which produces fused imidazoles,... 

The reaction of a-azidoketones with triphenylphosphine has recently been reported to give pyrazines in good yields. In this manner 2,5-diphenylpyiazine (307) was obtained in 75% yield from phenacyl azide. The reaction probably proceeds by dimerization followed by oxidation... 

The preparation of 22 was accomplished by a sequence involving the sodium borohydride reduction of phenacyl azide, followed by the conversion of the resulting azidohydrin to the azidochloride, which was then subjected to base-catalysed elimination (equation 5). 

Cleavage of C-N bonds has been described elsewhere, for example, the reduction of g wj-dinitroalkanes to nitrite ion and nitroalkane anion [181,182] and f-nitroalkanes to nitrite and alkyl radical (Chapter 9) and the reduction of pyridylamines to picoline and ammonia (Chapter 18) [13,14] a rare case of a reductive loss of a nitro group from a benzene ring in l,2,4,5-tetrafluoro-3,6-dinitrobenzene has been reported [183]. Reduction of activated azides yields azide ion phenacyl azide is thus reduced to acetophenone and azide [236]. 

GA4-17-S-propyl-S-phenacyl azide (structure I, Fig. 3) induces a-amylase in aleurone protoplasts (Fig. 1), although it is less active than the parent compound (GA4). In aqueous solution it has a X ax of294 nm (Fig. 2). Solutions are stable in the dark but are photolyzed within seconds of exposure to intense light of wavelengths above 300 nm (Fig. 2). Aryl azides photolyse to highly reactive aryl nitrenes that can covalently attach to amino acids at the binding site. See [15] for a detailed. account of the reactions of aryl nitrenes. 

Fig. 1. Dose response curves of GA and GA -IT-S-propyl-S-phenacyl azide (structure I, Fig. 3) in aleurone protoplasts...

Preparation by adding dropwise triethylamine and acetyl chloride to a solution of o-hydroxy-phenacyl azide in THF at 0-5°, then at r.t. for 1 h (95%) [6143]. 

M. Keshavarz, R. Badri, A fficile and one pot synthesis of l,4-disubstituted-lH-l,2,3-triazoles from terminal alkynes and phenacyl azides prepared from styrenes by CAN oxidant and sodium azide. Mol. Divers. 15 (2011) 957-962. 

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