Single and double reductive cleavage of C-O bonds of aromatic dimethyl acetals and ketals: Generation of benzylic mono- and dicarbanions

Article abstract of DOI:10.1016/S0040-4039(00)73488-5

The reductive cleavage of aromatic dimethyl acetals and ketals, 1, with Li metal in THF at low temperature allows the generation of stable α-alkoxy-α-arylsubstituted carbanions, avoiding the Wittig rearrangement. Reaction of these carbanions with various electrophiles afforded the expected products 2. Further in situ reaction of compounds 2 afforded the products of reductive electrophilic disubstitution, 3.