Sulfonic acid azides

The y-nitrogen atom of a sulfonic acid azide is electrophilic and reacts in an electrophilic aromatic substitution with an activated benzene or naphthalene derivative, e.g., a phenoxide ion, forming a l-tosyl-3-aryltriazene (2.47). The 1,4-quinone diazide is obtained by hydrolysis (Scheme 2-30, Tedder and Webster, 1960). The general applicability of this reaction seems to be doubtful. With 1-naphthol the 1,2-naphthoquinone diazide was obtained, not the 1,4-isomer. 

The so-called transdiazotizations are mechanistically related to the introduction of diazonio groups using sulfonic acid azides. An aromatic diazonium ion forms a triazene (diazoamino compound) with an aromatic amine the triazene tautomerizes and dissociates at the Na-Np bond of the original diazonium ion. This reaction is important for the synthesis of the 4-aminobiphenyl-4,-diazonium ion, which cannot be obtained by direct (mono-)diazotization of 4,4 -diaminobiphenyl (Allan and... 

Aryl chloride Aryl iodide Aryl selenic acid Aryl sulfonic acid Azide... 

Bis(trimethylsilyl)diazene (BSD), Me3Si—N=N—SiMe3, may be prepared easily by oxidation of lithium tris(trimethylsilyl)hydrazide (1) with appropriate oxidizing agents. The BSD so formed does not oxidize further to molecular nitrogen, for example with Br2, HgO, or EtOOC—N=N— COOEt. Nearly quantitative yields of BSD have been obtained by reaction of 1 with sulfonic acid azides, R S02N3 (R = phenyl or p-tolyl) in ether at -78°C (23) [Eq. (1)]. By analogy with reaction of arenesulfonic acid azides... 

Sulfonic acid azides from sulfonic acid chlorides SOgCl SO2N3... 

Irradiation isopropanol Sulfonic acid amides from sulfonic acid azides... 

Benzenesulfonyl azide Reactions of N-heterocyclics with sulfonic acid azides N-Condensed 1,2,3-triazoIe ring... 

N-Sulfonylaziridine ring from sulfonic acid azides s. 22, 123 s. a. A. I. Meyers, D. M. Stout, and T. Takaya, Chem. Commun. 1972, 1260 reactions with azido-pentafluorobenzene s. R. E. Banks and A. Prakash, Tetrah. Let. 1973, 99... 

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