Side-chain bromination and acetoxylation of alkylaroms. by halide ion-induced decompn. of K2S2O8 in AcOH were studied by product anal. Catalytic amts. of LiBr in the presence of NaOAc were effective in promoting benzylic bromination, followed by conversion to the corresponding benzyl acetates by reaction with acetate. The reaction occurs via a redox and free-radical chain mechanism involving Br• atoms (ρ = -1.38 vs. σ+ for substituted toluenes). In competitive expts., benzyl and 4-nitrobenzyl acetates were less reactive than the corresponding toluenes in AcOH with the couple S2O82-/Br-, but more reactive in CCl4 with NBS
Benzylic bromination-acetoxylation of toluenes by bromide ion-catalyzed thermal decomposition of peroxydisulfate in acetic acid in the presence of acetate ions
CITTERIO, ATTILIO;
1987-01-01
Abstract
Side-chain bromination and acetoxylation of alkylaroms. by halide ion-induced decompn. of K2S2O8 in AcOH were studied by product anal. Catalytic amts. of LiBr in the presence of NaOAc were effective in promoting benzylic bromination, followed by conversion to the corresponding benzyl acetates by reaction with acetate. The reaction occurs via a redox and free-radical chain mechanism involving Br• atoms (ρ = -1.38 vs. σ+ for substituted toluenes). In competitive expts., benzyl and 4-nitrobenzyl acetates were less reactive than the corresponding toluenes in AcOH with the couple S2O82-/Br-, but more reactive in CCl4 with NBS| File | Dimensione | Formato | |
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