Lewis acid promoted reactions (iv)lab oxidation deprotection of trimethylsilyl ethers with silver and sodium bromates; agbr03, nabr03

Abstract

Primary and secondary benzylic and saturated trimethylsilyl ethers are converted to their carbonyl compounds with AgBrO3 IAICI3 efficiently. p-Hydroquinonetrimethylsilyl ether is also converted with both AgBrO3 IAlCl3 and NaBrO3 IAlCl3 to p-benzoquinone. AgBrO3IAlCl3 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 NaBrO3IAlCl3; AgBrO3 is more efficient and selective oxidant than NaBrO3. © 1994, Taylor & Francis Group, LLC. All rights reserved.