Journal of the American Chemical Society

An Attempted Fries Reaction with Thiolesters. The Formation of Trithioörthoesters1

DS Tarbell, AH Herz

Index: Tarbell; Herz Journal of the American Chemical Society, 1953 , vol. 75, p. 1668,1670

Full Text: HTML

Citation Number: 11

Abstract

The Fries rearrangement of favorably substituted aryl thiolesters has not been realized, even in the presence of the strong Lewis acid, aluminum bromide. Instead, trithioorthoesters may be formed by partial cleavage of the thiolester, followed by the addition of the thiophenol to the ester carbonyl. Thus, phenyl thiolacetate upon treatment with boron fluoride or aluminum bromide yielded phenyl trithiolirthoacetate (I). Structure I had been previously assigned to ...

Related Articles:

The reaction of thioesters with nitriles. A new synthetic approach to the preparation of substituted 4-alkylthio-and 4-arylthiopyrimidine derivatives

[Herrera, Antonio; Martinez-Alvarez, Roberto; Ramiro, Pedro Tetrahedron, 2003 , vol. 59, # 37 p. 7331 - 7336]

The reaction of thioesters with nitriles. A new synthetic approach to the preparation of substituted 4-alkylthio-and 4-arylthiopyrimidine derivatives

[Herrera, Antonio; Martinez-Alvarez, Roberto; Ramiro, Pedro Tetrahedron, 2003 , vol. 59, # 37 p. 7331 - 7336]

One-step synthesis of complex cyclopropanone phenylthioketals by the reaction of sulfur-stabilized anions with ketene bis (phenylthio) acetal

[Cohen,T. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 25 p. 4744 - 4746]

Anhydrous hydrogen fluoride catalyzed Friedel-Crafts reactions of thioaromatic compounds

[Aslam, Mohammad; Davenport, Kenneth G.; Stansbury, Wayne F. Journal of Organic Chemistry, 1991 , vol. 56, # 20 p. 5955 - 5958]

Carbanion-Bildung aus Estern der Orthothiokohlensäure durch nukleophile Substitution an Schwefel

[Wildschut,G.A. et al. Monatshefte fuer Chemie, 1967 , vol. 98, p. 1043 - 1049]

More Articles...