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Effect of reaction conditions and substrate structure on direction of adding bromomalonic ester to α,β-unsaturated aldehydes

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

Conclusions

  1. 1.

    The use of the K2CO3-DMF-TEBAC system instead of NaOH-CH2Cl2-TEBAC-for running the reaction of bromomalonic ester with 3,3-dichloroacrolein and 5,5-dichloro-2,4-pentadienal changes the direction of the reaction and leads to obtaining the oxide (Darzens reaction product) instead of the cyclopropane (Michael reaction product).

  2. 2.

    On the example of arylidenemalonic aldehydes, we discovered a new type of adding bromomalonic ester under two-phase conditions (K2C03-DMF-TEBAC) to give dihydrofurans.

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Literature cited

  1. T. Warner and O. A. Moe, J. Am. Chem. Soc,70., 3470 (1948).

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  5. Z. Arnold, V. Kral, and D. Dvorak, Tetrahedron Lett., 1725 (1982).

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Authors and Affiliations

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

    Z. Arnold, V. Kral, G. V. Kryshtal & L. A. Yanovskaya

  2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czechoslovak SSR, Prague

    Z. Arnold, V. Kral, G. V. Kryshtal & L. A. Yanovskaya

Authors
  1. Z. Arnold
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  2. V. Kral
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  3. G. V. Kryshtal
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  4. L. A. Yanovskaya
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2162–2165, September, 1983.

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Arnold, Z., Kral, V., Kryshtal, G.V. et al. Effect of reaction conditions and substrate structure on direction of adding bromomalonic ester to α,β-unsaturated aldehydes. Russ Chem Bull 32, 1954–1957 (1983). https://doi.org/10.1007/BF00954686

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  • DOI: https://doi.org/10.1007/BF00954686

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