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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 ]
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.
It is a self-sustaining sequence in which the resulting products continue to propagate further reactions. [1] Examples of chain reactions in living organisms are lipid peroxidation in cell membranes [2] and propagation of excitation of neurons in epilepsy. [3]
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.
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 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]
A recyclable polymeric phosphine ligand is obtained from ring-opening metathesis polymerization of a norbornene derivative, and has been used in the copper co-catalyzed Sonogashira reaction of methyl p-iodobenzoate and phenylacetylene using Pd(dba) 2 ·CHCl 3 as a palladium source. [38]
The reaction proceeds via a Diels-Alder reaction to give the hexaphenyldienone, which then eliminates carbon monoxide. [ 1 ] Together with 1,2,3,4-tetraphenylnaphthalene, hexaphenylbenzene forms by the chromium-catalyzed oligomerization of diphenylacetylene . [ 3 ]
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