ChemInform Abstract: Reaction of Dilithiated Carboxylic Acids with Iodine: Evidence for the Formation of a Radical Anion Intermediate.

ChemInform Abstract

Several carboxylic acids are converted to the corresponding dianions by treatment with two equivalents of LDA or BuLi. Subsequent addition of iodine or electrolytic oxidation induces dimerization. The dialkylacetic acids (I) form the succinic acids (II), together with the iodides (III). Electrolysis of the dianions derived from the phenylacetic acids (IV) yields the symmetrical (V) and/or asymmetrical dicarboxylic acids (VI). Cyclopropylacetic acid (VII) gives the iodinated derivative (VIII), together with the dimer (X) and the cleavage product (IX). (Further examples and mechanistic discussions in the original paper).