TY - JOUR
T1 - Preparation and reductive decomposition of 2-iodoxybenzenesulfonic acid. X-ray crystal structure of 1-hydroxy-1H-1,2,3-benziodoxathiole 3,3-dioxide
AU - Koposov, Alexey Y.
AU - Litvinov, Dmitry N.
AU - Zhdankin, Viktor
AU - Ferguson, Michael J.
AU - McDonald, Robert
AU - Tykwinski, Rik R.
PY - 2006/10/27
Y1 - 2006/10/27
N2 - 2-Iodoxybenzenesulfonic acid (in a cyclic tautomeric form of 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide), a thiaanalog 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 1-hydroxy-1H-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, 1-hydroxy-1H-1,2,3-benziodoxathiole 3,3-dioxide (the cyclic tautomeric form of 2-iodosylbenzenesulfonic acid), was established by single-crystal X-ray diffraction.
AB - 2-Iodoxybenzenesulfonic acid (in a cyclic tautomeric form of 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide), a thiaanalog 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 1-hydroxy-1H-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, 1-hydroxy-1H-1,2,3-benziodoxathiole 3,3-dioxide (the cyclic tautomeric form of 2-iodosylbenzenesulfonic acid), was established by single-crystal X-ray diffraction.
KW - Hypervalent compounds
KW - Iodine
KW - Oxidation
KW - X-ray diffraction
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U2 - 10.1002/ejoc.200600683
DO - 10.1002/ejoc.200600683
M3 - Article
AN - SCOPUS:33750851168
SN - 1434-193X
SP - 4791
EP - 4795
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 21
ER -