A very facile S(sub N)Ar reaction with elimination of methoxide

The substrate system, 1-benzoyl-4-methoxynaphthalene, was utilized to elucidate S(sub N)Ar reactions. When reacted with dimethyl sulphoxide and potassium hydroxide, the product contained around 10% 18O, as evidenced by mass spectrometry data. The findings are in good agreement with only the reactions of S(sub N)Ar in which hydroxide acts as the nucleophile and methoxide as the nucleofuge.