Isolation and characterization of episulfoxides

✍ Scribed by Kiyosi Kondo; Akira Negishi; Masaru Fukuyama

• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 200 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88190-9

✦ Synopsis

In a recent communication, Hartzell and Paige (1) reported that the sodium metaperiodate oxidation of ethylene episulfide in aqueous methanol g8ve the oorrezponding episulfoxide. This method, however, afforded impure materials in low yields when appl%ed to the syntheses of substituted ones and the identification of the products w8z rather obsoure. Ye now wish to describe the isolation and speotrosoopio characterization of sever81 epieulfoxides which were obtained by perbenzoic 8oi.d oxidation of episulfides in non-aqueous solvents.

A solution of episulfide in methylene chloride was treated with an equimolar 8meunt of perbenzoic acid (2) at -20 to -30'. Usually, oxidation ~8s completed in a few minutez.

The simultaneously formed benzoic acid ~8s transformed to its ammonium salt by flashing dry ammonia on the surfaoe of the reaction mixture and eesily removed by filtrstion.

Evapor8tion of the solvent afforded almost pure episulfoxidee, which were purified by appropriate methods depending on the nature of the products (vide infr8).