Anionic σ-complexes of 1,3,5-tris(fluorosulfonyl)benzene

Despite 1,3,5-tris(fluorosulfonyl)benzene 1 being a strong aromatic sulfonic-acid halide it is able to undergo nucleophilic addition at the free positions of aromatic ring with the formation of relatively stable anionic σ-complexes 3–8. We have found that symmetrical benzene trisulfonic-acid trifluo...

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Bibliographic Details
Published in:Tetrahedron letters 2008-04, Vol.49 (17), p.2719-2721
Main Authors: Boiko, Vladimir N., Kamoshenkova, Oksana M., Filatov, Andrey A.
Format: Article
Language:English
Subjects:
1,3,5-Tris(fluorosulfonyl)benzene
Anionic σ-complexes
Aromatic nucleophilic addition
Aromatic sulfonic-acid fluorides
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Summary:Despite 1,3,5-tris(fluorosulfonyl)benzene 1 being a strong aromatic sulfonic-acid halide it is able to undergo nucleophilic addition at the free positions of aromatic ring with the formation of relatively stable anionic σ-complexes 3–8. We have found that symmetrical benzene trisulfonic-acid trifluoride 1 is able to undergo nucleophilic addition at free positions on the aromatic ring. Its reactions with sodium sulfite, morpholine and carbanions of malonic and acetoacetic esters, dimedone and nitromethane lead to the formation of comparatively stable anionic σ-complexes 3–8.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.02.151