66050-67-7Relevant academic research and scientific papers
Reactions of Phenyl(styryl)iodonium Tetrafluoroborate with Halide Ions
Okuyama, Tadashi,Oka, Hsjime,Ochiai, Masahito
, p. 1915 - 1921 (1998)
Reactions of (E)-phenyl(styryl)iodonium tetrafluoroborate with chloride, bromide, and iodide ions are examined under various conditions. The products are those of substitution and elimination, involving (Z)-1-halo-2-phenylethene (2), phenylacetylene (3), and iodobenzene as main products as well as minor products of (E)-2 and 1-halo-1-phenylethene. Results of product analysis, UV absorption spectroscopy, and kinetic measurements are consistent with major pathways involving pre-equilibrium formation of halo-λ3-iodane and iodate intermediates, leading to the in-plane vinylic SN2 substitution to (Z)-2 and the intramolecular β-elimination to 3. The minor retained product (E)-2 is concluded to be formed through the vinylenebenzenium ion intermediate in 2,2,2-trifluoroethanol through the ligand coupling within the λ3iodane intermediate in acetonitrile. 1-Bromo-1-phenylethene is considered to be derived from 3 by reaction with HBr formed during the reaction.
In situ generation of vinyl allenes and its applications to one-pot assembly of cyclohexene, cyclooctadiene, 3,7-nonadienone, and bicyclo[6.4.0]dodecene derivatives with palladium-catalyzed multicomponent reactions
Lee, Phil Ho,Lee, Kooyeon,Kang, Youngjin
, p. 1139 - 1146 (2006)
A novel tandem Pd-catalyzed cross-coupling and [4 + 4] cycloaddition sequence allows the rapid synthesis of eight-membered carbocycles starting from α-bromovinyl arenes and propargyl bromides in one reaction vessel. It is noteworthy that four components a
