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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 ]
Some examples include: The coupling of 2-iodoprop-2-en-1-ol with a wide range of acetylenes. [52] The preparation of alk-2-ynylbuta-1,3-dienes from the cross-coupling of a diiodide and phenylacetylene, as shown below. [53] Synthesis of an alk-2-ynylbuta-1,3-diene accomplished by Sonogashira coupling. [53]
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]
In the propagation phase, the lipid radical reacts with oxygen (O 2) or a transition metal, forming a peroxyl radical (LOO •). This peroxyl radical continues the chain reaction by reacting with a new unsaturated fatty acid, producing a new lipid radical (L •) and lipid hydroperoxide (LOOH). These primary products can further decompose into ...
Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenation. [3] 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.
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These reactions invariably involve metal-acetylide intermediates. This reaction was discovered by chemist John Ulric Nef in 1899 while experimenting with reactions of elemental sodium, phenylacetylene, and acetophenone. [3] [4] For this reason, the reaction is sometimes referred to as Nef synthesis.