Lewis Acid Promoted Reactions. (IV.)^1a,b Oxidation Deprotection of Trimethylsilyl Ethers with Silver and Sodium Bromates; AgBrO₃, NaBrO₃

Abstract

Primary and secondary benzylic and saturated trimethylsilyl ethers are converted to their carbonyl compounds with AgBrO₃/AlCl₃ efficiently. p-Hydroquinonetrimethylsilyl ether is also converted with both AgBrO₃/AlCl₃ and NaBrO₃/AlCl₃ to p-benzoquinone. AgBrO₃/AlCl₃ is also able to oxidize primary trimethylsilyl ethers to their carboxylic acids. Primary and secondary benzylic trimethylsilyl ethers are also converted to their carbonyl compounds with NaBrO₃/AlCl₃; AgBrO₃ is more efficient and selective oxidant than NaBrO₃.