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Synlett 1995; 1995(1): 113-115
DOI: 10.1055/s-1995-4848
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An Unusual Rearrangement Leading to Ortho-Thiomethylation of Arylacetic Acid Derivatives

Manuel Bourgaux, Anne-Françoise Gillet-Berwart, Jacqueline Marchand-Brynaert, Léon Ghosez*
  • *Laboratoire de Chimie Organique de Synthèse, Université Catholique de Louvain, Place Louis Pasteur 1, B-1348 Louvain-La-Neuve, Belgium
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Publication History

Publication Date:
31 December 2000 (online)

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Arylacetic esters 1 are converted into the corresponding ketene acetals 2 by O-silylation. Compounds 2 smoothly rearrange in refluxing THF to give the ortho-thiomethylated arylacetic acids 4 after hydrolysis. The sequence can be performed with good yields (63-81%) as a one-pot process.

ortho-thiomethylation - sigmatropic rearrangement - arylacetic esters - ketene acetals