- Trimethylsilyl directed aromatic sulfonation with sulfur trioxide- dioxane complex
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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 electron rich aromatic rings, but fails in the case of aromatic rings substituted by groups such as a carboxylate. Aromatic heterocycles form sulfur trioxide complexes which deactivate them to substitution.
- Wuts, Peter G. M.,Wilson, Katherin E.
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- N-Alkylation of N-trimethylsilyl derivatives of lactams, amides, and imides with alkyl sulfonates
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The reaction of N-trimethylsilyl derivatives of amides and imides with alkyl sulfonates on heating affords the corresponding N-alkyl derivatives and trimethylsilyl sulfonates.
- Baukov, Yu. I.,Kramarova, E. P.,Negrebetsky, Vad. V.,Shagina, A. D.,Shipov, A. G.,Tarasenko, D. V.
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p. 398 - 400
(2020/04/15)
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- Sulfosilylation of Aromatic Hydrocarbons by Trimethylsilyl Chlorosulfonate
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Aromatic hydrocarbons 2 ,6 ,8 ,9 ,13 ,16 ,18 ,19 ,22 react with trimethylsilyl chlorosulfonate (1) to give trimethylsilyl arenesulfonates 5, 7, 11, 12, 15, 23 or sulfonic acids 17, 20, 21.If trimethylsilyl sulfonates are obtained, working up of the sulfonation mixtures is possible by distillation.By hydrohalogenolysis of trimethylsilyl sulfonates 5 at 0-5 deg C anhydrous sulfonic acids 3 result.The pathways to diphenylsulfone (25a) in the reaction of benzene (2a) with 1 were investigated.In this connection we succeeded in synthesizing benzenepyrosulfonic acid (28) and trimethylsilyl benzenepyrosulfonate (29).
- Hofmann, Karin,Simchen, Gerhard
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p. 282 - 297
(2007/10/02)
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