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Mechanism of nucleophilic substitution in O,O-dimethyl-O-(4-nitrophenyl)thiophosphate in micellar solutions of 2-hydroxyethyldimethyloctadecylammonium bromide

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

The mechanism of nucleophilic substitution in O,O-dimethyl-O-(4-nitrophenyl)-thiophosphate (DNTP) has been studied in alkaline micellar solutions of cationic 2-hydroxyethyl surfactant which displays nucleophilic properties on account of dissociation of the 2-hydroxyethyl group. Further transformation of the intermediate product formed can take place by regeneration of the initial nucleophilic form of the surfactant, or by formation of a new zwitterion form of phosphorylated surfactant.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Academy of Sciences of the USSR, USSR

    E. P. Tishkova, S. B. Fedorov, L. A. Kudryavtseva, V. E. Bel'skii, I. É. Ismaev & B. E. Ivanov

Authors
  1. E. P. Tishkova
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  2. S. B. Fedorov
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  3. L. A. Kudryavtseva
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  4. V. E. Bel'skii
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  5. I. É. Ismaev
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  6. B. E. Ivanov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 902–905, April, 1991.

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Tishkova, E.P., Fedorov, S.B., Kudryavtseva, L.A. et al. Mechanism of nucleophilic substitution in O,O-dimethyl-O-(4-nitrophenyl)thiophosphate in micellar solutions of 2-hydroxyethyldimethyloctadecylammonium bromide. Russ Chem Bull 40, 800–803 (1991). https://doi.org/10.1007/BF00958577

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  • DOI: https://doi.org/10.1007/BF00958577

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