The selective functionalization of saturated hydrocarbons. Part 44. Measurement of size of reagent by variation of steric demands of competing substrates using Gif chemistry.

Cyclohexane has been co-oxidized with a number of aromatic compounds of varying steric requirements. The oxidant was hydrogen peroxide with Fe(III)-picolinic acid in a Gif type solvent of pyridine and acetonitrile. Both the cyclohexane and the aromatic derivatives were reacting with the same iron species. From the steric requirements for the hydroxylation of the aromatic partner, it can be deduced that the iron species is of significant size. For this reason, and also because of known pulse radiolysis results, hydroxyl radicals are not involved. (C) 1998 Elsevier Science Ltd. All rights reserved.