79756-86-8Relevant academic research and scientific papers
The concerted addition of HBr to aryl alkynes; orthogonal pi bond selectivity
Weiss, Hilton M.,Touchette, Kim M.,Angell, Sarah,Khan, Jihan
, p. 2152 - 2156 (2007/10/03)
In a weakly acidic solution, the addition of HBr to 1-phenylprop-1-yne produces predominantly the anti-Markovnikov product. In this paper, we consider five possible explanations for this behavior and conclude that the concerted addition is occurring on the acetylenic π bond orthogonal to the extended aromatic π system. The electronic effect of the distal methyl group and the steric hindrance of the coplanar phenyl ring combine to promote bromide attack at the β carbon. Attack on this π bond is insensitive to the electronic effect of meta and para substituents on the ring but is very (sterically) sensitive toward all ortho substituents.
Alkyne metathesis with simple catalyst systems: High yield dimerization of propynylated aromatics; scope and limitations
Pschirer, Neil Gregory,Bunz, Uwe H. F.
, p. 2481 - 2484 (2007/10/03)
High yield dimerization of propynylated benzenes and propynylnaphthalene by a mixture of Mo(CO)6 and 4-chlorophenol at 140 °C in 1,2-dichlorobenzene is reported to give the corresponding disubstituted alkynes. The scope and limitation of the reaction and the influence of substitution pattern and substitution type are discussed. Oxygen or nitrogen carrying substrates metathesize in moderate to good yields and ortho-alkyl substituted examples form the respective tolanes very efficiently.
Choix des methodes pour la synthese univoque de carbures acetyleniques. Troisieme partie : Arylacetylenes et aryl-1 alcynes-1
Mesnard, Danielle,Bernadou, Francoise,Miginiac, Leone
, p. 3216 - 3245 (2007/10/02)
The range of applicability of six syntheses of pure alkynes with one aryl group has been defined; a short review of other possible procedures is included.We have specified the best method to obtain selectively the alkynes Ar-CCH and Ar-CC-R, according to the nature of the substituents of the aryl group and according to the developed structure of the R group.It is thus possible to recommend with the largest probability of success the method to obtain, in homogenous series, alkynes corresponding to still more complicated structures.
