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Synthesis and valence isomerization of δ-dimethylamino-γ-chlorodienones to 2-dimethylamino-3-chloro-2h-pyrans1H and13C NMR and UV spectroscopic study

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

Conclusions

  1. 1.

    The aminal and aminalacetal of α-chloro-β-dimethylaminoacrolein were synthesized and their reactions with ketones and β-dicarbonyl compounds were investigated.

  2. 2.

    Dienylic δ-dimethylamino-γ-chloroketones, ketoesters, and diesters were obtained.

  3. 3.

    Dynamic equilibria between δ-dimethylamino-γ-chlorodienones and the corresponding 3-chloro-2-dimethylamino-2H-pyrans are established as a result of valence isomerization.

  4. 4.

    The position of the dienone-2H-pyran equilibrium depends upon the solvent. An increase in the specific solvating ability of the solvent shifts the equilibrium in favor of the δ-aminodienone form.

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Literature cited

  1. Zh. A. Krasnaya, E. P. Prokof'ev, and V. F. Kucherov, Izv. Akad. Nauk. SSSR, Ser. Khim., 123 (1978).

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  4. A. S. Dvornikov, Zh. A. Krasnaya, and Ya. N. Malkin, Izv. Akad. Nauk SSSR, Ser. Khim., 390 (1981).

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Authors and Affiliations

  1. N. D. Zelinski Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    Zh. A. Krasnaya, T. S. Stytsenko, V. S. Bogdanov, E. D. Daeva & A. S. Dvornikov

Authors
  1. Zh. A. Krasnaya
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  2. T. S. Stytsenko
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  3. V. S. Bogdanov
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  4. E. D. Daeva
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  5. A. S. Dvornikov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1075–1090, May, 1985.

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Krasnaya, Z.A., Stytsenko, T.S., Bogdanov, V.S. et al. Synthesis and valence isomerization of δ-dimethylamino-γ-chlorodienones to 2-dimethylamino-3-chloro-2h-pyrans1H and13C NMR and UV spectroscopic study. Russ Chem Bull 34, 978–994 (1985). https://doi.org/10.1007/BF01142787

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  • DOI: https://doi.org/10.1007/BF01142787

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