- Cleavage of sulfonamides with phenyldimethylsilyllithium
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The toluene-p-sulfonamides of secondary amines and indoles are cleaved by treatment with phenyldimethylsilyllithium to give the secondary amines. Aziridine toluene-p-sulfonamides, however, are opened by attack of the silyllithium reagent on carbon to give β-silylethyl sulfonamides. The aziridine toluene-p-sulfonamide 22 derived from norbornene is different in giving the 2-[dimethyl(phenyl)silyl]-4-methylbenzenesulfonamide 23 of exo-norbornylamine. The aziridine toluene-p-sulfonamides 26, 28 and 30, derived from methyl cinnamate, methyl acrylate and cinnamyl acetate, are also anomalous, giving 3-[N-(p-tolylsulfonyl)amino]-3-phenylpropionic acid 27, {3-[N-(p-tolylsulfonyl)amino]propionyl}-dimethyl(phenyl)silane 29 and trans-cinnamyl alcohol 31, respectively, each derived by opening of the aziridine ring followed by loss of the silyl group.
- Fleming, Ian,Frackenpohl, Jens,Ila, Hiriyakkanavar
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p. 1229 - 1235
(2007/10/03)
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- Substitution at Tetracoordinate Sulfur(VI). Rearrangement of 2-Aminoaryl Arenesulfonates to N-(2-Hydroxyaryl)arenesulfonamides
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A series of eight 2-aminoaryl arenesulfonates upon treatment by strong bases rearranged intramolecularly to their corresponding N-(2-hydroxyaryl)arenesulfonamides as did the related tosylates derived from 2-amino-3-hydroxypyridine, 1-amino-2-naphthol, and
- Andersen, Kenneth K.,Gowda, Gopala,Jewell, Linda,McGraw, Phillip,Phillips, Brian T.
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p. 1884 - 1889
(2007/10/02)
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