TRIMETHYLSILYL DIRECTED AROMATIC SULFONATION WITH SULFUR TRIOXIDE-DIOXANE COMPLEX

Authors
WUTS PGM WILSON KE
Citation
Pgm. Wuts et Ke. Wilson, TRIMETHYLSILYL DIRECTED AROMATIC SULFONATION WITH SULFUR TRIOXIDE-DIOXANE COMPLEX, Synthesis, (11), 1998, pp. 1593-1595
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
11
Year of publication
1998
Pages
1593 - 1595
Database
ISI
SICI code
0039-7881(1998):11<1593:TDASWS>2.0.ZU;2-5
Abstract
A mild procedure for trimethylsilyl group directed sulfonation through ipso aromatic substitution has been developed using in situ generated sulfur trioxide-dioxane complex. The process is effective with electr on rich aromatic rings, but fails in the case of aromatic rings substi tuted by groups such as a carboxylate. Aromatic heterocycles form sulf ur trioxide complexes which deactivate them to substitution.