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

Koposov Alexey Y. | Zendy; Litvinov Dmitry N. | Zendy; Zhdankin Viktor V. | Zendy; Ferguson Michael J. | Zendy; McDonald Robert | Zendy; Tykwinski Rik R. | Zendy

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

Author(s) -

Koposov Alexey Y.,

Litvinov Dmitry N.,

Zhdankin Viktor V.,

Ferguson Michael J.,

McDonald Robert,

Tykwinski Rik R.

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200600683

Subject(s) - chemistry , tautomer , oxidizing agent , reagent , decomposition , crystal structure , hydrolysis , medicinal chemistry , single crystal , organic chemistry , polymer chemistry , crystallography

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)

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