Diazenes. II. Preparation of Phenyldiazene

Pih Kuei C. Huang, Edward M. Kosower

Research output: Contribution to journalArticlepeer-review

Abstract

The preparation of phenyldiazene (phenyldiimide), C6H6N=NH (3), by decarboxylation of phenyldiazenecarboxylate anion, C6H6N=NCOO- (2), is described. All work was carried out in oxygen-free systems because of the sensitivity of 3 to oxygen. The proof of structure of 3 depends upon (1) method of generation, (2) ultraviolet-visible spectra (very similar to that of C6H5N=NCH3), (3) reduction to phenylhydrazine, and (4) volatility. Phenyldiazene is the first monosubstituted diazene to be directly observed and characterized.

Original languageEnglish
Pages (from-to)2362-2367
Number of pages6
JournalJournal of the American Chemical Society
Volume90
Issue number9
DOIs
StatePublished - Apr 1968
Externally publishedYes

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