Metalation of Arylmethyl Methyl Ethers and Connection with Their Reductive Electrophilic Substitution

Article abstract of DOI:10.1016/00404-0399(50)1035G-

Stable α-methoxy arylmethyl carbanions can be generated by metalation of arylmethyl methyl ethers, 1, with n-BuLi in THF at -40 degC, avoiding Wittig rearrengement to the corresponding alkoxides 2.Reaction of these carbanions with various electrophiles afforded the expected products 3 in satisfactory yields.Connection between the metalation procedure and the reductive electrophilic substitution of arylmethyl methyl ethers allowed the transformation of compounds 1 into 2-arylpropanoic acids, 5.