Diazo Compounds


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Diazo Compounds

 

the general name for organic substances that contain a group of two atoms of nitrogen bound to one carbon atom; essentially, the term “diazo compounds” applies to various classes of compounds. The structure of acyclic diazo compounds may be represented by the following formulas:

Acyclic diazo compounds decompose on heating, on exposure to ultraviolet radiation, in the presence of catalysts such as copper and its salts (which results in the formation of carbenes), and in the presence of acids. Diazomethane and ethyl diazoacetate are typical representatives of this class of compounds. Acyclic cyclodiazo compounds (diazirines),

Diazo Compounds, are more stable and less reactive than true

acyclic diazo compounds: they form carbenes upon pyrolysis or photolysis but do not react with acids or unsaturated compounds.

Another class of diazo compounds is represented by diazonium salts, which form upon diazotization of aromatic amines. Aromatic diazo compounds are unstable, and dry compounds are explosive; they enter into many reactions. Diazotates are formed in the presence of alkalies. Aromatic diazo compounds are intermediate products of the production of azo dyes and other organic substances. Photosensitive aromatic diazo compounds are used extensively in the diazo process.

REFERENCES

D’iakonov, I. A. Alifaticheskie diazosoedineniia. Leningrad, 1958.
Zollinger, H. Khimiia azokrasitelei. Leningrad, 1960. (Translated from German.)
Dinaburg, M. S. Svetochuvstvitel’nye diazosoedineniia i ikh primenenie. Moscow-Leningrad, 1964.

B. L. DIATKIN

References in periodicals archive ?
Bagheri, "Highly effective catalytic methods for ylide generation from diazo compounds. Mechanism of the rhodium- and copper-catalyzed reactions with allylic compounds," Journal of Organic Chemistry, vol.
Linear free energy relationships in catalyzed decompositions of diazo compounds and CO and isonitrile complexation," Journal of the American Chemical Society, vol.
Li's team used the same catalyst system with a slightly different base to couple aryl amidines 39 and diazo compounds 40 to deliver five examples of monofluorinated and trifluoromethylated 1-aminoisoquinolines 41 in fair to excellent yields [37].
His highly original studies of the reactions of between organoboranes and diazo compounds led to the development of new methods for the preparation of several classes of compounds: ketones, esters, aldehydes, nitriles; all involving the formation of new carbon-carbon bonds.
Chemical engineers of course know the hazard potential of the most popular substances such as peroxides, organic nitro and diazo compounds and certain mixtures (ie.