Diazodiphenylmethane Explained

Diazodiphenylmethane is an organic reagent with the chemical formula C13H10N2. It exists as red-black crystals that melts just above room temperature.[1]

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.[2] An improved procedure involves dehydrogenation with oxalyl chloride.[3]

Uses

It can be used to synthesise (diphenyl)methyl esters and ethers with carboxylic acids and alcohols respectively.[4] [5]

It can also generate the (diphenyl)methyl carbene and nitrogen gas upon illumination by ultraviolet light or heating.[6] [7] 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.[8]

Notes and References

  1. Web site: Diphenyldiazomethane;1,1'-(Diazomethylene)bisbenzene;Diazodiphenylmethane,physical properties,suppliers,CAS,MSDS,structure,Molecular Formula, Molecular Weight,Solubility,boiling point, melting point . chemyq.com . 2016-06-06 . dead . https://web.archive.org/web/20160804033036/http://chemyq.com/En/xz/xz1/8364rohuk.htm . 2016-08-04 .
  2. Miller. J. 1959-04-01. Notes- Preparation of Crystalline Diphenyldiazomethane. The Journal of Organic Chemistry. 24. 4. 560–561. 10.1021/jo01086a603. 0022-3263.
  3. Web site: orgsyn.org/demo.aspx?prep=V85P0189. orgsyn.org. 2017-03-11.
  4. Jovanovic . Bratislav . Assaleh . Fathi . Marinkovic . Aleksandar . Kinetics of the reaction of 5-substituted orotic acids with diazodiphenylmethane . https://web.archive.org/web/20200213142816/http://www.doiserbia.nb.rs/Article.aspx?ID=0352-51390411949J . dead . 2020-02-13 . Journal of the Serbian Chemical Society . 69 . 11 . 949–953 . 10.2298/jsc0411949j . 2004 . free .
  5. Petursson. Sigthor. 2003-04-22. Tin(II) chloride catalyzed reactions of diazodiphenylmethane with vicinal diols in an aprotic solvent. The reactions with cis- and trans-1,2-cyclohexanediols and 1,2-propanediol. Carbohydrate Research. 338. 9. 963–968. 10.1016/S0008-6215(03)00039-9.
  6. Parker. Vernon D.. Bethell. Donald. 1987-08-01. Carbene cation radicals: the kinetics of their formation from diazoalkane cation radicals and their reactions. Journal of the American Chemical Society. 109. 17. 5066–5072. 10.1021/ja00251a002. 0002-7863.
  7. Book: Sabongi, Gebran J.. Chemical Triggering: Reactions of Potential Utility in Industrial Processes. 2012-12-06. Springer Science & Business Media. 9781461309079. en.
  8. McDonald. Richard N.. Triebe. F. M.. January. J. R.. Borhani. K. J.. Hawley. M. D.. 1980-12-01. Hypovalent radicals. 6. Electroreduction of diazodiphenylmethane - intermediacy of Ph2CN2-.cntdot. and Ph2C-.cntdot.. Journal of the American Chemical Society. 102. 27. 7867–7872. 10.1021/ja00547a007. 0002-7863.

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