Preparation and Reductive Decomposition of 2-Iodoxybenzenesulfonic Acid. X-ray Crystal Structure of 1-Hydroxy-1H-1,2,3-benziodoxathiole 3,3-Dioxide

✍ Scribed by Alexey Y. Koposov; Dmitry N. Litvinov; Viktor V. Zhdankin; Michael J. Ferguson; Robert McDonald; Rik R. Tykwinski

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 118 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200600683

✦ Synopsis

Abstract

2‐Iodoxybenzenesulfonic acid (in a cyclic tautomeric form of 1‐hydroxy‐1__H__‐1,2,3‐benziodoxathiole 1,3,3‐trioxide), a thia‐analog of 2‐iodoxybenzoic acid (IBX) and a potentially important oxidizing reagent, was prepared by two different pathways: direct oxidation of 2‐iodobenzenesulfonic acid and hydrolysis of the methyl ester of 2‐iodylbenzenesulfonic acid. The resulting l‐hydroxy‐1__H__‐1,2,3‐benziodoxathiole 1,3,3‐trioxide was found to be thermally unstable and highly reactive towards organic solvents. The structure of its reductive decomposition product, l‐hydroxy‐1__H__‐1,2,3‐benziodoxathiole 3,3‐dioxide (the cyclic tautomeric form of 2‐iodosylbenzenesulfonic acid), was established by single‐crystal X‐ray diffraction.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)