Diazodiphenylmethane is an

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reagent with the chemical formula C₁₃H₁₀N₂. It exists as red-black crystals that melts 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

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catalyst. An improved procedure involves dehydrogenation with oxalyl chloride.

Uses

It can be used to synthesise (diphenyl)methyl esters and ethers with

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s and

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s respectively. It can also generate the (diphenyl)methyl carbene and nitrogen gas upon illumination by ultraviolet light or heating. It can also be electrolysed to form the Ph₂CN anion, which can decompose to form the Ph₂C⁻ anion radical. If carried out in dimethylformamide and tetrabutylammonium perchlorate, these can react to form benzophenone azine, which has the formula Ph₂C=N-N=CPh₂.

References

{{Reflist Diazo compounds Phenyl compounds