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Novel C-phosphorylated heterodienes based on pentachloroethyl isocyanate

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Abstract

A preparative method for the synthesis of novel N-phosphorylcarbonyl-and N-alkoxycarbonyltrichloroacetimidoylphosphonates from accessible pentachloroethyl isocyanate was developed. Factors that determine the C/N-selectivity of the phosphorylation of trichloroacetimidoyl chlorides were revealed: phenyl substituents at the P atom and an electron-withdrawing N-alkoxycarbonyl group in imidoyl chloride favored N-phosphorylation, while reactions with silyl phosphite gave exclusively C-phosphorylation products.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, 5 ul. Murmanskaya, 02094, Kiev, Ukraine

    Yu. V. Rassukana, A. A. Sinitsa & P. P. Onys’ko

Authors
  1. Yu. V. Rassukana
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  2. A. A. Sinitsa
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  3. P. P. Onys’ko
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Dedicated to the Corresponding Member of the Russian Academy of Sciences T. A. Mastryukova.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2563–2566, November, 2005.

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Rassukana, Y.V., Sinitsa, A.A. & Onys’ko, P.P. Novel C-phosphorylated heterodienes based on pentachloroethyl isocyanate. Russ Chem Bull 54, 2648–2651 (2005). https://doi.org/10.1007/s11172-006-0170-x

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  • DOI: https://doi.org/10.1007/s11172-006-0170-x

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