Facile access to 2-acyloxy-, aryloxy- and alkenyloxy-2: H -azirines via an SN2′-SN2′ cascade in 2-halo-2 H -azirines

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Abstract

Various 2-oxygen-substituted 2H-azirine-2-carboxylic acid derivatives were synthesized in high yields under mild conditions from readily available precursors, 2-halo-2H-azirines and OH-reagents having pKa values in the range of 3-10. This reaction is the first example of substitution at the azirine carbon atom for which an unusual SN2′-SN2′ cascade mechanism was revealed.

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Rostovskii, N. V., Smetanin, I. A., Agafonova, A. V., Sakharov, P. A., Ruvinskaya, J. O., Khlebnikov, A. F., & Novikov, M. S. (2018). Facile access to 2-acyloxy-, aryloxy- and alkenyloxy-2: H -azirines via an SN2′-SN2′ cascade in 2-halo-2 H -azirines. Organic and Biomolecular Chemistry, 16(17), 3248–3257. https://doi.org/10.1039/c8ob00553b

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