Tetrahedron Letters

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

Full Text: HTML

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.

Related Articles:

Reaktionen der Trialkylsilyl??trifluormethansulfonate, I. Synthese von Trialkylsilyl??Enolethern

[Emde, Herbert; Goetz, Andreas; Hofmann, Karin; Simchen, Gerhard Liebigs Annalen der Chemie, 1981 , # 9 p. 1643 - 1657]

Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensation

[Heathcock, Clayton H.; Buse, Charles T.; Kleschick, William A.; Pirrung, Michael C.; Sohn, John E.; Lampe, John Journal of Organic Chemistry, 1980 , vol. 45, # 6 p. 1066 - 1081]

Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensation

[Heathcock, Clayton H.; Buse, Charles T.; Kleschick, William A.; Pirrung, Michael C.; Sohn, John E.; Lampe, John Journal of Organic Chemistry, 1980 , vol. 45, # 6 p. 1066 - 1081]

More Articles...