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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]
The reaction was discovered in 1884 by Swiss chemist Traugott Sandmeyer, when he attempted to synthesize phenylacetylene from benzenediazonium chloride and copper(I) acetylide. Instead, the main product he isolated was chlorobenzene . [ 5 ]
Phenylacetylene; Calicene, or triapentafulvalene; Cubene This page was last edited on 6 March 2021, at 06:43 (UTC). Text is available under the Creative Commons ...
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]
The dipyrimidyl-palladium complex shown below has been employed in the copper-free coupling of iodo-, bromo-, and chlorobenzene with phenylacetylene using N-butylamine as base in THF solvent at 65 °C. Furthermore, all structural features of this complex have been characterized by extensive X-ray analysis, verifying the observed reactivity. [39]
This page was last edited on 18 November 2018, at 03:11 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may apply.
The trimethylsilyl group can then be cleaved off with TBAF or DBU to form phenylacetylene derivatives. [1] Trimethylsilylacetylene is also used to synthesize diphenylacetylene derivatives in a one-pot Sonogashira coupling, in which the phenylacetylene derivative reacts with a second aryl halide after in-situ deprotection. [ 2 ]