METALATION REACTIONS. VII. METALATION OF BENZYLALKYL AND β-PHENETHYLALKYL SULFIDES

Article abstract of DOI:10.1016/S0022-328X(00)87069-2

The products from the reaction between n-butyllithium and benzylalkyl and β-phenethylalkyl sulfides followed by carbonation, have been investigated by GLC/MS analysis.With benzylalkyl sulfides metalation occurs at the benzylic position, and the corresponding carboxylic acid can be isolated, but side products from Wittig like rearrangement, cleavage of the thioether bond, and aliphatic and aromatic substitution are also obtained.No benzylic metalation or Wittig-like rearrangement products are obtained from β-phenethyl sulfides: instead cleavage of the thioether bond and aliphatic and aromatic substitution occur.