Diazodiphenylmethane is an organic reagent with the chemical formula C13H10N2. It exists as red-black crystals that melt just above room temperature.
Preparation Diazodiphenylmethane can be synthesized via the oxidation of benzophenone hydrazone with mercury(II) oxide in diethyl ether and the presence of a basic catalyst. An improved procedure involves dehydrogenation with oxalyl chloride.
Uses Like all diazo compounds, diazodiphenylmethane is an alkylating agent, forming diphenylmethyl esters and ethers with carboxylic acids and alcohols, respectively.
When heated or illuminated with ultraviolet light, the compound decomposes, forming (diphenyl)methyl carbene and nitrogen gas. Electrolytic reduction in dimethylformamide with tetrabutylammonium perchlorate cosolute generates the Ph2CN radical anion, which also loses N2. The resulting Ph2C− radical anion can attack other molecules of diazodiphenylmethane to form benzophenone azine, which has the formula Ph2C=N-N=CPh2.
References