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Unusual Transformations of Allylsilanes in the Reaction with N,N-Dichloroarenesulfonamides

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Abstract

The reactions of allyl(chloromethyl)dimethylsilane, diallyl(dimethyl)silane, and diallyl(diphenyl)­silanes with N,N-dichloroarenesulfonamides have been studied. Due to the presence of active chlorine atoms in the reagents, the reactions with allyl(chloromethyl)dimethylsilane gave the corresponding chloroamination products, whereas 1-(arenesulfonyl)-4-chloro-1,2-azasilolidines and 1-[(4-chlorobenzenesulfonyl]-5,5-di­phenyl-1,4,5,6-tetrahydro-1,5-azasilocine were formed in moderate yields in the reactions with diallylsilanes.

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ACKNOWLEDGMENTS

This study was performed using the facilities of the Baikal joint analytical center, Siberian Branch, Russian Academy of Sciences.

Funding

This work was financially supported by the Russian Science Foundation (project no. 22-13-00036).

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Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    I. V. Ushakova & B. A. Shainyan

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  1. I. V. Ushakova
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  2. B. A. Shainyan
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Correspondence to I. V. Ushakova.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 7, pp. 904–909 https://doi.org/10.31857/S0514749223070042.

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Ushakova, I.V., Shainyan, B.A. Unusual Transformations of Allylsilanes in the Reaction with N,N-Dichloroarenesulfonamides. Russ J Org Chem 59, 1144–1148 (2023). https://doi.org/10.1134/S1070428023070047

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