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Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane

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Abstract

The reaction of trimethyl(vinyl)silane with sulfonamides in the presence of N-bromosuccinimide was shown to proceed regioselectively in methylene chloride under mild conditions and led to the products of bromosulfamidation in up to 88% yield. The obtained adducts undergo base-promoted dehydrobromination to give 2-trimethylsilyl-N-sulfonyl aziridines in a close to quantitative yield. In the reaction with trifluoromethanesulfonamide in acetonitrile or tetrahydrofuran, the Ritter-type (solvent-interception) products were obtained and converted to 1-triflyl-2-methyl-5-(trimethylsilyl)-2-imidazoline or 4-triflyl-3-(trimethylsilyl)-1,4-oxazocane in almost quantitative yield.

Graphical abstract: Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane

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Publication details

The article was received on 31 Jul 2019, accepted on 09 Aug 2019 and first published on 09 Aug 2019


Article type: Paper
DOI: 10.1039/C9OB01689A
Org. Biomol. Chem., 2019, Advance Article

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    Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane

    V. V. Astakhova, M. Yu. Moskalik and B. A. Shainyan, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01689A

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