Thallium in organic synthesis. 61. Intramolecular capture of radical cations from thallium (III) trifluoroacetate oxidation of arylalkanoic acids and arylalkanols. New …

EC Taylor, JG Andrade, GJH Rall…

Index: Taylor, Edward C.; Andrade, Juan G.; Rall, Gerhardus J. H.; Turchi, Ignatius J.; Steliou, Kosta; et al. Journal of the American Chemical Society, 1981 , vol. 103, # 23 p. 6856 - 6863

Full Text: HTML

Citation Number: 23

Abstract

Abstract: Treatment of electron-rich arylpropionic acids with TTFA in TFA containing a small amount of BF3. etherate results in the formation of dihydrocoumarins and spirocyclohexadienone lactones by initial formation of aromatic radical cations followed by intramolecular cyclization involving the side-chain carboxyl group. The scope and limitations of this reaction with respect to aromatic substitution and the length of the alkanoic acid ...