INTRAMOLECULAR SELECTIVITY IN THE SIDE-CHAIN OXIDATION OF ALKYLBENZENES UNDER GIFIV CONDITIONS

The intramolecular selectivity in the side-chain oxidation of alkylbenzenes, under the Gif(IV) conditions, has been determined. The 1-degrees-C:2-degrees-C:3-degrees-C reactivity ratios are 1:5:9.3 and little difference in reactivity is exhibited by methyl groups para and meta to 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 Fe(III). The catalyzed pathway is particularly effective towards towards secondary positions, as expected in Gif(IV)-promoted oxidations.