NOVEL CONVERSION OF AROMATIC ESTER GROUPS TO METHYL - CATALYTIC EFFECT OF IODINE IN REACTIONS INVOLVING IODOTRIMETHYLSILANE

A three-step sequential procedure has been developed whereby a “one-pot” reduction of aromatic ester groups direct ly to methyl is now possible. One of these steps involves conversion of the aromatic ester to a trimethylsilyloxy ester by means of iodotrimethylsilane or one of its variants. A strong catalytic effect by iodine in reactions involving iodotrimethylsilane has been discovered. The intermediacy of trimethylsilyl triiodide is proposed to explain certain spectral effects noted in the NMR. Iodine catalysis also permits an alternative suggestion as to the reason for the superiority of trimethylphenylsilane-iodine combinations as a substitute for iodotrimethylsilane itself. © 1979, American Chemical Society. All rights reserved.