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Double Arbuzov Reaction. Synthesis of Bis(ω-cyanoalkyl)phosphinic Acids

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Abstract

A general method for the synthesis of symmetric bis(ω-cyanoalkyl)phosphinic acids from ammonium hypophosphite was proposed. The reaction of bis(trimethylsilyl)hypophosphite generated in situ with the ω-bromoalkylnitrile molecule according to the Arbuzov reaction and the subsequent silylation of the hydrophosphoryl intermediate leads to the formation of bis(trimethylsilyl)phosphonite. The latter reacts with the second ω-haloalkylnitrile molecule by the Arbuzov reaction with the formation of the second phosphorus-carbon bond.

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References

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Funding

This work was financially supported by the Presidium of the Russian Academy of Sciences (Program no. 14), the Russian Foundation for Basic Research (grants no. 18-03-00959, 18-03-01123) and the Russian Science Foundation (grant no. 19-13-00294, chromatographic, spectral and elemental analysis) within the frame of governmental task for the Institute of Physiologically Active Substances of the Russian Academy of Sciences for 2019.

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Authors and Affiliations

  1. Institute of Physiologically Active Substances of the Russian Academy of Sciences, Severnyi proezd 1, Chernogolovka, 142432, Russia

    V. V. Ragulin

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  1. V. V. Ragulin
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Correspondence to V. V. Ragulin.

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Conflict of Interest

No conflict of interest was declared by the authors.

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 8, pp. 1305–1308.

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Ragulin, V.V. Double Arbuzov Reaction. Synthesis of Bis(ω-cyanoalkyl)phosphinic Acids. Russ J Gen Chem 89, 1728–1730 (2019). https://doi.org/10.1134/S1070363219080292

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  • DOI: https://doi.org/10.1134/S1070363219080292

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