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Thermolysis of dimethyl cis- and trans-1 pthalimidoaziridine-2,3-dicarboxylates in the presence of dipolarophiles

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Abstract

Thermolysis of dimethyl esters of stereoisomeric phthalimidoaziridine-2,3-dicarboxylic acids in the presence of dimethyl fumarate, dimethyl maleate, and N-phenylmaleimide occurred stereo-specifically and stereoselectively led to the formation of derivatives of 1-phthalimidopyrrolidine, products of 1,3-dipolar additrion of intermediately arising azomethine ylides. In keeping with the rules of the conservation of orbital symmetry the thermal opening of the 2,3-disubstituted 1-phthalimidoaziridines into azomethine ylides occurred conrotatory. The relative positions of the substituents in the dipolarophiles is retained in the reaction products indicating the concerted addition mechanism.

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References

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Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, 198504, Russia

    M. A. Kuznetsov, A. V. Ushkov, S. I. Selivanov & A. S. Pan’kova

  2. Organisch-chemisches Institut der Universität Zürich, Zürich, Switzerland

    A. Linden

Authors
  1. M. A. Kuznetsov
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  2. A. V. Ushkov
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  3. S. I. Selivanov
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  4. A. S. Pan’kova
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  5. A. Linden
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Corresponding author

Correspondence to M. A. Kuznetsov.

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Original Russian Text © M.A. Kuznetsov, A.V. Ushkov, S.I. Selivanov, A.S. Pan’kova, A. Linden, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 8, pp. 1209–1216.

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Kuznetsov, M.A., Ushkov, A.V., Selivanov, S.I. et al. Thermolysis of dimethyl cis- and trans-1 pthalimidoaziridine-2,3-dicarboxylates in the presence of dipolarophiles. Russ J Org Chem 45, 1200–1207 (2009). https://doi.org/10.1134/S1070428009080144

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  • DOI: https://doi.org/10.1134/S1070428009080144

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