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Interaction of the 2-monoanil of 1,3-diphenyl-1,2,3-propanetrione with trimethyl phosphite and tris(dimethylamino)phosphine

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

Conclusions

  1. 1.

    Trimethyl phosphite reacts with the 2-monoanil of 1,3-diphenyl-1,2,3-propanetrione under mild conditions to form 2,2,2-trimethoxy-3,5-diphenyl-4-benzoyl-1,3,2-oxazaphospholene (II).

  2. 2.

    Hydrolysis of (II) gives N-dibenzoylmethyl N-phenyl OO-dimethyl amidophosphate (IV). We have examined its keto-anol tautomerism.

  3. 3.

    Compound (IV) is also formed by reaction of (I) with trimethyl phosphite in the presence of acetic acid.

  4. 4.

    Tris(dimethylamino)phosphine reacts with the 2-monoanil of 1,3-diphenyl-1,2,3-propanetrione to form a dipolar 1∶1 adduct (III) with a P-N bond.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 608–611, March, 1979.

We thank É. I. Gol'dfarb and R. G. Gainullina for recording the PMR and31P NMR spectra.

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Polezhaeva, N.A., Agafonov, M.N. & Arbuzov, B.A. Interaction of the 2-monoanil of 1,3-diphenyl-1,2,3-propanetrione with trimethyl phosphite and tris(dimethylamino)phosphine. Russ Chem Bull 28, 562–564 (1979). https://doi.org/10.1007/BF00924833

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  • DOI: https://doi.org/10.1007/BF00924833

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