Abstract
Relative reactivity values in benzylic bromination of alkylbenzenes and benzyl type ethers by 4-bromo-2,4,6-tri-t-butyl-2,5-cyclohexadienone (BTBC) have been measured by intermolecular competition with benzhydryl methyl ether as reference standard at 40° in CCl 4 are compared with results found for N-bromosuccinimide (NBS). The reactivity values for m- and p-substituted XC 9H 4CH 2OMe relative to this standard toward BTBC show a polar effect with ϱ = −0·43 correlated by σ + constants; a result identical to that found for NBS (ϱ = −0·45) carried out in CH 2Cl 2. The identical ϱ-values and other data support the suggestion that atomic Br is the main H-abstracting species in benzylic bromination using BTBC.
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