In the presence of {[K.18-Crown-6]Br3}n, a unique tribromide reagent, trimethylsilyl (TMS) ethers, tetrahydropyranyl (THP) ethers, and alcohols were oxidized to their corresponding aldehydes and ketones in H2O2. One-pot deprotection and oxidation of TMS ethers/THP ethers were performed directly and the conversion was complete. Avoiding the isolation of the corresponding alcohol as an intermediate step, the direct transformation of such substrates to carbonyls is the main aim of this work. {[K.18-Crown-6]Br3}n regeneration was performed via the addition of Br2 to the residue of the reaction and recrystallization in acetonitrile.
