Radical-chain isomerisation of allyl silyl ethers to silyl enol ethers in the presence of thiols as polarity reversal catalysts
AJ Fielding, BP Roberts
Index: Fielding, Alistair J.; Roberts, Brian P. Tetrahedron Letters, 2001 , vol. 42, # 24 p. 4061 - 4064
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Citation Number: 19
Abstract
The radical-chain isomerisation of allyl silyl ethers to silyl enol ethers takes place on heating in the presence of an initiator and an arenethiol as a protic polarity reversal catalyst; pentafluorothiophenol is particularly effective in this role. The reaction complements the transition-metal-catalysed isomerisation and could be useful for the preparation of silyl enol ethers from readily available allylic alcohols.
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