Intramolecular Selectivity in the Side-Chain Oxidation of Alkylbenzenes Under GifIV Conditions.

Abstract The intramolecular selectivity in the side-chain oxidation of alkylbenzenes, under the GifIV conditions, has been determined. The 1°-C: 2°-C: 3°-C reactivity ratios are 1:5: 9.3 and little difference in reactivity is exhibited by methyl groups para and meta to a chloro substituent. It has also been found that these selectivities result from the operation of two competing oxidations pathways, one of which not requiring catalysis by FeIII. The catalyzed pathway is particularly effective towards secondary positions, as expected in GifIV-promoted oxidations.