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Yet another method involves the coupling of iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling. The related Sonogashira coupling involves the coupling of iodobenzene and phenylacetylene. Diphenylacetylene is a planar molecule. The central C≡C distance is 119.8 picometers. [1]
Phenylacetylene is a prototypical terminal acetylene, undergoing many reactions expected of that functional group. It undergoes semi hydrogenation over Lindlar catalyst to give styrene . In the presence of base and copper(II) salts, it undergoes oxidative coupling to give diphenylbutadiyne . [ 6 ]
A 3D model of ethyne (), the simplest alkyneIn organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. [1] The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula C n H 2n−2.
In organic chemistry, syn-and anti-addition are different ways in which substituent molecules can be added to an alkene (R 2 C=CR 2) or alkyne (RC≡CR). The concepts of syn and anti addition are used to characterize the different reactions of organic chemistry by reflecting the stereochemistry of the products in a reaction.
Anti-Markovnikov behaviour is observed in the hydration of phenylacetylene by auric catalysis, which gives acetophenone; although with a special ruthenium catalyst [8] it provides the other regioisomer 2-phenylacetaldehyde: [9] Anti-Markovnikov hydration. Anti-Markovnikov behavior can also manifest itself in certain rearrangement reactions.
The chemical structure of the para-phenylene group.. In organic chemistry, the phenylene group (−C 6 H 4 −) is based on a di-substituted benzene ring ().For example, poly(p-phenylene) is a polymer built up from para-phenylene repeating units. [1]
It is a member of the diyne chemical class and can be made via the Glaser coupling of phenylacetylene [2] However, a variety of other synthesis methods have been developed. [3] [4] Diphenylbutadiyne forms a variety of metal-alkyne complexes. One example is the organonickel complex (C 5 H 5 Ni) 4 C 4 (C 6 H 5) 2. [5]
The reaction was discovered in 1884 by Swiss chemist Traugott Sandmeyer, when he attempted to synthesize phenylacetylene from benzenediazonium chloride and copper(I) acetylide. Instead, the main product he isolated was chlorobenzene . [ 5 ]