A convenient synthetic route to 2,4,6-tris(chlorosulfonyl)- and 2,4,6-tris(fluorosulfonyl)phenol, aniline and chlorobenzene |
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Authors: | Vladimir N. Boiko Andrey A. Filatov Yurii L. Yagupolskii Wieland Tyrra Dieter Naumann Ingo Pantenburg Hendrik T.M. Fischer Frank Schulz |
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Affiliation: | aInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanskaya St., UA-02094, Kiev 94, Ukraine;bInstitut für Anorganische Chemie, Universität zu Köln, Greinstrasse 6, D-50939 Köln, Germany |
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Abstract: | Convenient and preparative synthetic procedures of 2,4,6-tris(chlorosulfonyl)- and 2,4,6-tris(fluorosulfonyl)phenol, -chlorobenzene and -aniline have been elaborated. Chlorine exchange for fluorine by KF interaction on 2,4,6-tris(chlorosulfonyl)aniline and especially 2,4,6-tris(chlorosulfonyl)phenol proceeds easily and selectively under anhydrous conditions in dioxane. Unlike, 2,4,6-tris(chlorosulfonyl)chlorobenzene transformation requires the presence of water. On the basis of 2,4,6-tris(fluorosulfonyl)phenol and some of its salts, XRD measurements demonstrated the structural similarity to picric acid and its derivatives in the solid state. |
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Keywords: | Arenes Sulfonylchlorides Sulfonylfluorides Nucleophilic substitution Synthetic methods Molecular structures |
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