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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]
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]
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.
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 .
The initial product is a thioamide for example that of acetophenone [7] which can again be hydrolyzed to the amide. The reaction is named after Karl Kindler The Kindler modification of the Willgerodt rearrangement. A possible reaction mechanism for the Kindler variation is depicted below: [8] The likely reaction mechanism for the Kindler ...
Iron has many existing roles in biology not related to redox reactions; examples include iron–sulfur proteins, hemoglobin, and coordination complexes. Iron has a widespread distribution globally and is considered one of the most abundant in the Earth's crust, soil, and sediments. [11] Iron is a trace element in marine environments. [11]
The Scholl reaction is a coupling reaction between two arene compounds with the aid of a Lewis acid and a protic acid. [1] [2] It is named after its discoverer, Roland Scholl, a Swiss chemist. The Scholl reaction. In 1910 Scholl reported the synthesis of a quinone [3] and of perylene from naphthalene [4] both with aluminum chloride.
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