ChemInform Abstract: Synthesis, Electrochemical, and Chemical Oxidations, and peri Selenium Participation of Macrocyclic Polyselenides Containing Naphthalene Rings.

✍ Scribed by H. FUJIHARA; M. YABE; N. FURUKAWA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199711149

✦ Synopsis

Synthesis, Electrochemical, and Chemical Oxidations, and peri Selenium Participation of Macrocyclic Polyselenides Containing Naphthalene Rings.

-New macrocyclic polyselenides (III), (VI), and (VIII) are prepared starting from naphthodiselenole (I). Hydrolysis of solutions of the bisand tris-selenide (III) and (VI), resp., in conc. H2SO4 provides stable monoselenoxides, whilst similar treatment of tetraselenide ( VIII) affords the ring-contracted products (III) and (IV). Moreover, the polyselenides are readily oxidized electrochemically. These facile reversible electrooxidations and the unusual stability of the corresponding cationic species are ascribed to the destabilization of the educts by transannular lone-pair-lone-pair repulsion and provable stabilization of the oxidized products by peri selenium participation.