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Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene [4] or BP) is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen (the site at which it is attached) may use the prefixes xenyl or diphenylyl .
The Zincke–Suhl reaction is a special case of a Friedel-Crafts alkylation and was first described by Theodor Zincke and Suhl in 1906. [1] [2] [3] Unlike the traditional Friedel-Crafts reaction, the reduction of the phenyl ring leads to a higher energy final product that can be used as starting material in the dienol–benzene rearrangement, among other reactions.
The most widely practiced example of this reaction is the ethylation of benzene. Approximately 24,700,000 tons were produced in 1999. [ 73 ] Highly instructive but of far less industrial significance is the Friedel-Crafts alkylation of benzene (and many other aromatic rings) using an alkyl halide in the presence of a strong Lewis acid catalyst.
It arises by a Friedel-Crafts-like reaction of sulfur monochloride and benzene. [4] Diphenyl sulfide and its analogues can also be produced by coupling reactions using metal catalysts. [5] It can also be prepared by reduction of diphenyl sulfone. [6] Diphenyl sulfide is a product of the photodegradation of the fungicide edifenphos. [7]
The methylene group in diphenylmethane is mildly acidic with a pK a of 32.2, and so can be deprotonated with sodium amide. [3](C 6 H 5) 2 CH 2 + NaNH 2 − → (C 6 H 5) 2 CHNa + NH 3. The resulting carbanion can be alkylated.
This group typically excludes compounds in which either benzene is fused to another ring (bicyclic, tricyclic, polycyclic) [1] or includes a heteroatom, or where the methane connects to three or four benzenes. Ball-and-stick model of the benzhydryl radical. The benzhydryl radical can be abbreviated Ph 2 CH• or Bzh. [2]
The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (−CH=O) or ketone (>C=O) reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group (C=O) is oxidized, and the hydrogen peroxide is reduced.
By the 1930s, focus had shifted to experimenting with the reactivity of meta-terphenyl and its potential use as a ligand. The first verified modified version of meta-terphenyl was created in 1932 by Arthur Wardner and Alexander Lowy and led to the creation of nitro-substituted meta-terphenyls as well as amino-meta-terphenyls from the oxidation of the nitro-substituted compounds. [9]