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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 ]
The Hay coupling is variant of the Glaser coupling. It relies on the TMEDA complex of copper(I) chloride to activate the terminal alkyne. Oxygen (air) is used in the Hay variant to oxidize catalytic amounts of Cu(I) to Cu(II) throughout the reaction, as opposed to a stoichiometric amount of Cu(II) used in the Eglington variant. [7]
It is advised to check the references for photos of reaction results. [1] Reagent testers might show the colour of the desired substance while not showing a different colour for a more dangerous additive. [2]
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Trimethylsilylacetylene is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, followed by reaction with trimethylsilyl chloride. [4] Trimethylsilylacetylene is a precursor to 1,4-bis(trimethylsilyl)buta-1,3-diyne, a protected form of 1,3-butadiyne. [5]
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]
In a classic example of click chemistry, phenyl azide and phenylacetylene react to give diphenyl triazole. Phenyl azide reacts with triphenylphosphine to give the Staudinger reagent triphenylphosphine phenylimide (C 6 H 5 NP(C 6 H 5) 3). Thermolysis induces loss of N 2 to give the highly reactive phenylnitrene C 6 H 5 N. [6]
Phenylacetylene was proven to form Pd monoacetylide complex D as well as Pd bisacetylide complex F under mild reaction conditions. Both activated species, namely complexes B and F , are involved in the transmetallation step, forming complex C and regenerating D .