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Reaction of dialkylphosphorous acids with 2-methylindane-1,3-dione

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

Conclusions

  1. 1.

    2-Methylindane-l,3-dione reacts with dialkylphosphorous acids in the presence of triethylamine at ∼20° with formation of 2-methyl-3-hydroxyindan-1-on-3-yl dialkylphosphonates. Upon further standing of the reaction mixture the latter isomerize to the corresponding phosphates.

  2. 2.

    2-Methyl-3-hydroxyindan-1-on-3-yl dialkylphosphonates upon reaction with thionyl chloride are transformed to 2-methylind-2-en-1-on-3-yl dialkylphosphonates.

  3. 3.

    Reaction of 2-methylindane-1,3-dione with diethylphosphorous acid in excess triethylamine at 160° proceeds complexly with formation of 2-methylind-2-en-1-on-3-yl diethylphosphate and a series of products not containing phosphorous. Unsaturated dialkyl phosphates were also obtained from 2-bromo-2-methylindane-1,3-dione and trialkyl phosphites.

  4. 4.

    2-Methylind-2-en-1-one reacts with diethylphosphorous acid in the presence of triethylamine with formation of 2-methyl-1-hydroxyind-2-en-1-yl diethylphosphonate.

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Literature cited

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Authors and Affiliations

  1. A. M. Butlerov Chemical Institute, USSR

    B. A. Arbuzov, N. P. Bogonostseva, V. S. Vinogradova & N. N. Batyrshin

  2. V. I. Ul'yanov-Lenin Kazan State University, USSR

    B. A. Arbuzov, N. P. Bogonostseva, V. S. Vinogradova & N. N. Batyrshin

Authors
  1. B. A. Arbuzov
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  2. N. P. Bogonostseva
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  3. V. S. Vinogradova
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  4. N. N. Batyrshin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1119–1124, May, 1976.

The authors express their gratitude to E. I. Gol'dfarb and R. Gainullin for taking NMR (H,31P) spectra.

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Arbuzov, B.A., Bogonostseva, N.P., Vinogradova, V.S. et al. Reaction of dialkylphosphorous acids with 2-methylindane-1,3-dione. Russ Chem Bull 25, 1088–1092 (1976). https://doi.org/10.1007/BF00921998

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  • DOI: https://doi.org/10.1007/BF00921998

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