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Unusual reactions of α-nitro-β-dimethylaminoacrolein

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

Conclusions

  1. 1.

    α-Nitro-β-dimethylaminoacrolein and the dimethylammonium salt of nitromalonaldehyde are readily interconvertible.

  2. 2.

    Condensation of α-nitro-β-dimethylaminoacrolein with dimedone in the presence of triethylamine is accompanied by deformylation with the formation of the dimethylammonium salt of nitroethylidenedimedone.

  3. 3.

    Condensation of α-nitro-β-dimethylaminoacrolein with ethyl acetoacetate in the presence of triethylamine, TEBA, or alumina gives methyl o-dimethylamino-m-nitrobenzoate together with the nitroethylidene derivative of ethyl acetoacetate, β-dimethylaminocrotonic ester, and 2-nitro-4-methoxy-carbonyl-5-dimethylaminohexa-2,4-dienal.

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Authors and Affiliations

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

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

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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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimcheskaya, No. 7, pp. 1604–1612, July, 1985.

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Krasnaya, Z.A., Stytsenko, T.S., Bogdanov, V.S. et al. Unusual reactions of α-nitro-β-dimethylaminoacrolein. Russ Chem Bull 34, 1468–1474 (1985). https://doi.org/10.1007/BF00950150

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  • DOI: https://doi.org/10.1007/BF00950150

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