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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 ]
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]
Cadiot–Chodkiewicz coupling; Cadogan-Sundberg indole synthesis; Camps quinoline synthesis; Cannizzaro reaction; Carbohydrate acetalisation; Carbonyl reduction
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]
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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.
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For example, acetylation of histones by histone acetyltransferases (HATs) results in an expansion of local chromatin structure, allowing transcription to occur by enabling RNA polymerase to access DNA. However, removal of the acetyl group by histone deacetylases (HDACs) condenses the local chromatin structure, thereby preventing transcription. [9]