Preparation and X-ray structure of 8,9,19,20-tetra hydrodinaphtho[1′,8′′jk; 1,8-bc][1,5,9,13]tetraselenacyclohexadecine, and its novel ring contraction in concentrated sulfuric acid
The novel title compound 1 has been synthesized; upon hydrolysis in sulfuric acid it gave ring-contracted products naphtho[1,8-bc]-1,5-diselenocin and its selenoxide.
Synthesis, electrochemical and chemical oxidations, and peri selenium participation of macrocyclic polyselenides containing naphthalene rings
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.