Abstract
Thermolysis of alk-1-enyl-N-phthalimidoaziridines leads to products of 1,5-electrocyclization of intermediate azomethine ylides with participation of C=C bonds. If acyl or alkoxycarbonyl substituent is present in the aziridine ring, the C=O bond is also involved. Thermolysis of the title compounds in the presence of N-phenylmaleimide or dimethyl acetylenedicarboxylate under analogous conditions gives products of 1,3-dipolar cycloaddition of azomethine ylides to the double or triple bond of the dipolarophile.
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Original Russian Text © M.A. Kuznetsov, V.V. Voronin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 1, pp. 91–100.
Dedicated to Full Member of the Russian Academy of Sciences G.A. Tolstikov on his 80th anniversary
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Kuznetsov, M.A., Voronin, V.V. Thermal transformations of alk-1-enyl-N-phthalimidoaziridines. Russ J Org Chem 49, 83–94 (2013). https://doi.org/10.1134/S1070428013010156
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DOI: https://doi.org/10.1134/S1070428013010156