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Diazo compounds have two linked nitrogen atoms (azo) as a terminal functional group. The general formula is R2C=N. e.g.: Diazomethane is a diazo compound. The first step of Arndt-Eistert synthesis involves the preparation of diazo ketone. Arndt-Eistert synthesis is a popular method of producing beta-amino acids from alpha-amino acids. In the presence of a nucleophile and a metal catalyst (Ag2O), diazoketones form the desired acid.
Diazo compounds behave as 1,3-dipoles in diazoalkane 1,3-dipolar cycloadditions. Diazo compounds can couple to form alkenes in carbene dimerization reactions. Diazo compounds can serve as carbene-precursors through thermolysis or photolysis in Wolf rearrangement, and produce ketenes, which in the presence of nucleophiles generate carboxylic acid derivatives. These ketenes are highly reactive species, and can be converted to large array of important compounds for example, generation of beta-lactams through [2+2] cycloaddition with imines (Staudinger Synthesis). Diazo compounds are involved in several important reactions, such as Buchner-Curtius-Schlotterbeck reaction, Bamford-Stevens reaction, Buchner ring expansion, and Doyle-Kirmse reaction.
Diazo compounds are not dyes, but they are dye precursors. Some azo dyes are manufactured by coupling a phenol or naphthol to a diazonium compound. In histotechnology, they are used to demonstrate the activity of some enzymes.