Lewis Acid Promoted Reactions. (IV.)1a,bOxidation Deprotection of Trimethylsilyl Ethers with Silver and Sodium Bromates; AgBrO3, NaBrO3
- 1 April 1994
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 24 (8) , 1065-1077
- https://doi.org/10.1080/00397919408011700
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.Keywords
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