An Unusual Rearrangement Leading To Ortho-thiomethylation of Arylacetic Acid-derivatives

Bourgaux, M.;Gilletberwart, AF.;Marchand-Brynaert, Jacqueline;Ghosez, Léon
(1995) Synlett : accounts and rapid communications in synthetic organic chemistry — n° 1, p. 113-115 (1995)

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  • Bourgaux, M.
    Author
  • Gilletberwart, AF.
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
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.
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Bourgaux, M., Gilletberwart, AF., Marchand-Brynaert, J., & Ghosez, L. (1995). An Unusual Rearrangement Leading To Ortho-thiomethylation of Arylacetic Acid-derivatives. Synlett : accounts and rapid communications in synthetic organic chemistry, 1, 113-115. https://doi.org/10.1055/s-1995-4848 (Original work published 1995)