Double Arbuzov Reaction. Synthesis of Bis(ω-cyanoalkyl)phosphinic Acids
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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.
KeywordsDouble Arbuzov reaction ammonium hypophosphite bis(trimethylsilyl)hypophosphite ω-haloalkylnitriles bis(ω-cyanoalkyl)phosphinic acids
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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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