26624-20-4Relevant articles and documents
Kinetic study on denomination of vic-dibromides with trivalent phosphorus compounds
Yasui, Shinro
, p. 217 - 222 (2007/10/03)
Various types of trivalent phosphorus compounds (I) brought about reductive debromination of vic-dibromides (2) to afford olefins. The reaction was accelerated by either electron-releasing substituents on the phosphorus of 1 or electron-with-drawing substituants on the α-carbon of 2. The substituent effects, along with the stereochemistry of the reaction, are consistent with an E1CB-like mechanism for the elimination of the two bromine atoms. That is, 1 initially undergoes nucleophilic attack upon a bromine of 2. At the transition state, a fractional positive charge is developed on the phosphorus of 1 and a fractional negative charge on the carbon of 2. This mechanism suggests the importance of an electronic character of the vic-dibromide in determining the relative ease of bromophilicity, carbophilicity, and basicity of the phosphorus of a trivalent phosphorus compound in a reaction with the dibromide. α 2001 John Wiley & Sons, Inc.
Selectivity Relationships and Substituent-Substituent Interactions in Carbocation-Forming Bromination. The Transition-State Contribution to the ρ Variation
Ruasse, Marie-Francoise,Argile, Alain,Dubois, Jacques-Emile
, p. 4846 - 4849 (2007/10/02)
For arylolefin bromination through benzylic carbocations, X-C6H4-C+(R)-CHBr-R', there are 18 reaction constants, ρR, describing ring-substituent effect X, which vary from -1.6 to -5.9 depending on R and R' (H, Me, OMe, or Ar').This r