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Article type: Research Article
Authors: Tsivgoulis, G.M. | Ioannou, P.V.
Affiliations: Department of Chemistry, University of Patras, Patras, Greece
Note: [] Corresponding author: P.V. Ioannou, Department of Chemistry, University of Patras, Patras, Greece. Fax: +30 2610 997118; E-mail: [email protected]
Abstract: The reaction of P(SPh)_{3}, As(SPh)_{3}, and Ph-As(SPh)_{2} with carboxylic acid anhydrides gives not only the thiol esters RCOSPh, but also the easily identified triphenyl phosphorotrithioate O=P(SPh)_{3}, diphenyl disulfide PhSSPh, and the anion RCOO^{-} in various proportions depending on the reaction conditions (in solution or neat at 120°C; in the absence and in the presence of an anhydride activator). The probable origin of the additional products is discussed.
Keywords: Triphenyl trithiophosphite, triphenyl trithioarsenite, diphenyl phenyldithioarsonite, carboxylic acid anhydrides, nucleophilicity, alpha effect
DOI: 10.3233/MGC-2010-0034
Journal: Main Group Chemistry, vol. 10, no. 1, pp. 51-62, 2011
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