Synthesis of [2.2]paracyclophane-pseudo-ortho-dicarboxylic acid

An efficient three-step synthesis of 2.2]paracyclophane-pseudo-ortho-dicarboxylic acid by dibromination of 2.2]paracyclophane, thermal isomerization of the resultingpseudopara-dibromide topseudo-ortho-isomer, followed by lithiation/carboxylation was developed. The possibility of preparation of two other novelpseudo-ortho-disubstituted carbonyl derivatives, 4-carboxy-12-(1-oxopenthyl)-2.2]paracyclophane and di(4-carboxy2.2]paracyclophanyl-12)ketone, was demonstrated when an excess of lithiation reagent (4 or 10 eq.) was used in the final step. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2001–2004, November, 1997.