Abstract
Thermolysis of trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile and trans-1-phthalimidoaziridine-2,3-dicarbonitrile in the presence of several dipolarophiles involves 1,3-dipolar cycloaddition to intermediate azomethine ylides and leads to 1-phthalimidopyrrolidine derivatives with good yields and high stereoselectivity. Thermally induced opening of the three-membered ring in trans-2,3-disubstituted 1-phthalimidoaziridines occurs in conrotatory mode to produce the corresponding cis-azomethine ylides in keeping with the orbital symmetry conservation rules. The relative configuration of substituents in the dipolarophiles is retained, which implies concerted mechanism of the addition.
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Original Russian Text © M.A. Kuznetsov, A.S. Pan’kova, A.V. Ushkov, S.I. Selivanov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 12, pp. 1807–1815.
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Kuznetsov, M.A., Pan’kova, A.S., Ushkov, A.V. et al. Thermolysis of 1-phthalimidoaziridine-2-carbonitriles in the presence of dipolarophiles. Russ J Org Chem 44, 1780–1788 (2008). https://doi.org/10.1134/S1070428008120105
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DOI: https://doi.org/10.1134/S1070428008120105