Tri??and Tetrasubstituted N??Phthalimidoaziridines in 1, 3??Dipolar Cycloaddition Reactions

…, MA Kuznetsov, A Linden, H Heimgartner

Index: Ushkov, Alexander V.; Kuznetsov, Mikhail A.; Linden, Anthony; Heimgartner, Heinz Helvetica Chimica Acta, 2010 , vol. 93, # 5 p. 847 - 862

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Citation Number: 5

Abstract

Abstract The thermal reactions of the 2, 2, 3-trisubstituted N-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 ...