Cleavages of ethers by chlorotrimethylsilane and acetic anhydride

doi:10.1016/S0040-4020(01)87555-4

Tetrahedron

Volume 42, Issue 14, 1986, Pages 3999-4006

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Abstract

Methyl and benzyl ethers have been cleaved with a combination of reagents consisting of chlorotrimethylsilane and acetic anhydride containing a catalytic amount of concentrated sulfuric acid. Methylthiomethyl ethers yield the corresponding acetoxymethyl ethers with chlorotrimethylsilane and acetic anhydride. Comparative study with the borontrifluoride etherate and acetic anhydride method of ether cleavage suggests that chlorotrimethylsilane and acetic anhydride (con. H₂SO₄ catalysis) could be a useful alternative to it.

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Citation Excerpt :
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Cleavages of ethers by chlorotrimethylsilane and acetic anhydride

Abstract

Tetrahedron Letters

J. Am. Chem. Soc.

J. Org, Chem.