Publication: Tri- and Tetra-Substituted N-Phthalimidoaziridines in 1,3-Dipolar Cycloaddition Reactions
Tri- and Tetra-Substituted N-Phthalimidoaziridines in 1,3-Dipolar Cycloaddition Reactions
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Ushkov, A. V., Kuznetsov, M. A., Linden, A., & Heimgartner, H. (2010). Tri- and Tetra-Substituted N-Phthalimidoaziridines in 1,3-Dipolar Cycloaddition Reactions. Helvetica Chimica Acta, 93(5), 847–862. https://doi.org/10.1002/hlca.200900466
Abstract
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Abstract
The thermal reactions of the 2,2,3-tri-substituted 1-phthalimidoaziridine 1a with dimethyl acetylenedicarboxylate (DMAD), thioketones 4a – 4d, and dimethyl azodicarboxylate (5) proceed even at room temperature leading to the five-membered cycloadducts 2a, 6 – 8, and 12, respectively, with retention of the spatial arrangement of the aziridine substituents, in contrast to the expectation based on the conservation of orbital symmetry in concerted reactions. The analogous reactions of the tetra-substituted phthalimidoaziridine 1b with thi
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- Ushkov, A V
- Kuznetsov, M A
- Heimgartner, H
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Ushkov, A. V., Kuznetsov, M. A., Linden, A., & Heimgartner, H. (2010). Tri- and Tetra-Substituted N-Phthalimidoaziridines in 1,3-Dipolar Cycloaddition Reactions. Helvetica Chimica Acta, 93(5), 847–862. https://doi.org/10.1002/hlca.200900466
