29624-17-7Relevant articles and documents
The functionalization of saturated hydrocarbons. Part 25. Ionic substitution reactions in GoAggIV chemistry: The formation of carbon-halogen bonds
Barton, Derek H. R.,Beviere, Stephane D.,Chavasiri, Warinthorn
, p. 31 - 46 (2007/10/02)
GoAggIV chemistry (Fe (III) species, tert-butyl hydroperoxide in a mixture of pyridine and acetic acid) in the presence of LiCl can transform saturated hydrocarbons efficiently into the corresponding alkyl chlorides. The transformation into monosubstituted alkyl derivatives by "ionic trapping" reagents arising from the interception of the first intermediate of the system supports the presence of a high valent VFe-C species. Mechanistic studies suggest a possible pathway operating via an Fe-centered ligand coupling. In addition, the production of alkyl chlorides and alkyl bromides could also be achieved employing this system in the presence of halogenating reagents such as CCl4 and BrCCl3.
Studies on the bromination of saturated hydrocarbons under GoAggIII conditions
Barton, Derek H. R.,Csuhai, Eva,Doller, Dario
, p. 3413 - 3416 (2007/10/02)
The bromination reaction of saturated hydrocarbons under GoAggIII conditons (FeCl3.6H2O picolinic acid, H2O2 in pyridine/acetic acid) and under radical chain conditions (dibenzoyl peroxide in pyridine/acetic acid or initiation by UV light) are compared. Differences in the selectivity and kinetic behavior for a series of polyhaloalkanes are in agreement with a non-radical mechanism for GoAggIII bromination. Comparison of the kinetic order of reactivity for a series of polyhaloalkanes under chain radical conditions and under GoAggIII conditions is in agreement with a non-radical reaction pathway for the Gif-type bromination reaction.
