Synthesis, electrochemical and chemical oxidations, and peri selenium participation of macrocyclic polyselenides containing naphthalene rings

Abstract

New macrocyclic polyselenides containing naphthalene rings 1–3 have been synthesized. The cyclic voltammograms of the selenides 1–3 show reversible oxidation peaks with remarkably low oxidation potentials. Hydrolysis of a solution of bis- and tris-selenides 1 and 2 in sulfuric acid gives the stable monoselenoxides 6 and 8. The peri interaction between the seleninyl and selanyl groups of 6 and 8 was identified by ⁷⁷Se NMR spectroscopy. In contrast to 1 and 2, the ring-contracted products are obtained from hydrolysis of a solution of 3 in sulfuric acid.