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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 ]
Trimerisation of unsymmetrical alkynes gives two isomeric benzenes. For example, phenylacetylene affords both 1,3,5- and 1,2,4-C 6 R 3 H 3. The substitution pattern about the product arene is determined in two steps: formation of the metallocyclopentadiene intermediate and incorporation of the third equivalent of alkyne.
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.
Chain reaction in chemistry and physics is a process that produces products capable of initiating subsequent processes of a similar nature. It is a self-sustaining sequence in which the resulting products continue to propagate further reactions. [1]
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]
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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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