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Synlett 1991; 1991(7): 501-502
DOI: 10.1055/s-1991-20777
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Preparation of tert-Butoxymethyl Phenyl Sulfone and Its Use in Synthesis as a Formyl Carbanion Equivalent

Fabrice Chemla* , Marc Julia, Daniel Uguen, Da Zhang
  • *Laboratoire de Chimie, Ecole Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France
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Publication Date:
07 March 2002 (online)

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tert-Butoxymethyl phenyl sulfone can be readily prepared, metalated and condensed with alkyl halides. The homologous 1-tert-butoxyalkyl phenyl sulfones can undergo hydrolysis under very mild conditions to give corresponding aldehydes or methanolysis to give dimethyl acetals. tert-Butoxymethyl phenyl sulfone thus acts as a formyl carbanion or dimethoxymethyl carbanion equivalent.