40193-73-5Relevant academic research and scientific papers
Ionic reaction of halogens with terminal alkenes: The effect of electron-withdrawing fluorine substituents on the bonding of halonium ions
Shellhamer, Dale F.,Allen, Jeannette L.,Allen, Rachel D.,Gleason, David C.,Schlosser, Colleen O'Neil,Powers, Benjamin J.,Probst, John W.,Rhodes, Michelle C.,Ryan, Andrew J.,Titterington, Peter K.,Vaughan, Gregory Gawayne,Heasley, Victor L.
, p. 3932 - 3937 (2007/10/03)
Ionic reactions of terminal alkenes with chlorine (Cl2), bromine (Br2), and iodine monochloride (ICI) are sensitive to the alkyl substituents, and the positions and number of vinyl fluorine atoms. These perturbations influence the symmetry of the halonium ion intermediates, which can be determined by the distribution of the Markovnikov to anti-Markovnikov products. A vinyl fluorine on the number-2 carbon favors an unsymmetrical intermediate with greater charge on the number-2 carbon unless the alkyl group is electron withdrawing. A vinyl fluorine on the terminal number-1 carbon favors positive charge development on that carbon unless a resonance stabilizing group is on the number-2 carbon. The symmetry of halonium ions with vinyl fluorines on both carbons-1 and -2 depends primarily on the characteristics of the alkyl substituent. Intermediates range from openions with the positive charge on carbon-2, to various bridged species, to open-ions on the terminal carbon.
Perhaloethyl aromatic compounds and perhaloethenyl aromatic compounds therefrom
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Example 1-2, (2008/06/13)
A synthesis is provided for α,β-difluoro-β-halo-ethenyl aromatic compounds such as α,β,β-trifluorostyrenes by a process of reacting CFX2CFXI, wherein each X is independently F or Cl, provided that at least one X is Cl and at least one X is F, with an aromatic compound Ar to form (CFX2CFX)n—Ar, wherein n is 1, 2 or 3, and subsequently dechlorohalogenating this product to form (CFX═CF)n—Ar. Novel synthetic intermediate compounds are provided.
