Radical-chain isomerisation of allyl silyl ethers to silyl enol ethers in the presence of thiols as polarity reversal catalysts

Alistair J. Fielding; Brian P. Roberts

doi:10.1016/S0040-4039(01)00630-X

Radical-chain isomerisation of allyl silyl ethers to silyl enol ethers in the presence of thiols as polarity reversal catalysts

Alistair J. Fielding, Brian P. Roberts

Research output: Contribution to journal › Article › peer-review

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. © 2001 Elsevier Science Ltd.

Original language	English
Pages (from-to)	4061-4064
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(01)00630-X
Publication status	Published - 11 Jun 2001

Keywords

Catalysis
Isomerisation
Radicals and radical reactions
Silicon and compounds
Thiols

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10.1016/S0040-4039(01)00630-X

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title = "Radical-chain isomerisation of allyl silyl ethers to silyl enol ethers in the presence of thiols as polarity reversal catalysts",

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. {\textcopyright} 2001 Elsevier Science Ltd.",

keywords = "Catalysis, Isomerisation, Radicals and radical reactions, Silicon and compounds, Thiols",

author = "Fielding, {Alistair J.} and Roberts, {Brian P.}",

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T1 - Radical-chain isomerisation of allyl silyl ethers to silyl enol ethers in the presence of thiols as polarity reversal catalysts

AU - Fielding, Alistair J.

AU - Roberts, Brian P.

PY - 2001/6/11

Y1 - 2001/6/11

N2 - 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. © 2001 Elsevier Science Ltd.

AB - 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. © 2001 Elsevier Science Ltd.

KW - Catalysis

KW - Isomerisation

KW - Radicals and radical reactions

KW - Silicon and compounds

KW - Thiols

U2 - 10.1016/S0040-4039(01)00630-X

DO - 10.1016/S0040-4039(01)00630-X

M3 - Article

SN - 1873-3581

VL - 42

SP - 4061

EP - 4064

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Radical-chain isomerisation of allyl silyl ethers to silyl enol ethers in the presence of thiols as polarity reversal catalysts

Abstract

Keywords

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