87018-36-8Relevant academic research and scientific papers
AN EFFICIENT METHOD FOR THE SYNTHESIS OF 1-ARYLALKYNES
Engler, Thomas A.,Combrink, Keith D.,Ray, James E.
, p. 1735 - 1744 (2007/10/02)
1-Arylalkynes are prepared from propiophenones in good yield via the sequence a) 2 equiv PCl5/Δ b) DBN or Δ and c) Mg metal.
Regio- and Stereochemistry of Bromochlorinations of Alkynes with molecular Bromine Chloride and Dichlorobromate(1-) Ion
Negoro, Takeshi,Ikeda, Yoshitsugu
, p. 3515 - 3518 (2007/10/02)
The bromochlorination of phenyl- and alkyl-substituted acetylenes with tetrabutylammonium dichlorobromate(1-) (1) in dichloromethane was found to be anti-stereospecific and nonregiospecific (regiospecific in the case of phenylacetylene).Whereas the addition of molecular bromine chloride (2) to phenyl-substituted acetylenes was found to give nonstereospecific and regiospecific adducts, the reaction of alkyl-substituted acetylenes gave anti-stereospecific and nonregiospecific adducts.These results suggest that the addition of 1 involves an attack of chloride ion to a three-centered ?-complex in the product-forming stage, and that the addition of 2 to phenyl-substituted acetylenes involves a vinyl cation intermediate (but a bridged bromonium ion intermediate in the case of alkyl-substituted acetylenes).
