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

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

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Publication details

The article was received on 05 Mar 2018, accepted on 06 Apr 2018 and first published on 06 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00553B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Facile access to 2-acyloxy-, aryloxy- and alkenyloxy-2H-azirines via an SN2′–SN2′ cascade in 2-halo-2H-azirines

    N. V. Rostovskii, I. A. Smetanin, A. V. Agafonova, P. A. Sakharov, J. O. Ruvinskaya, A. F. Khlebnikov and M. S. Novikov, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00553B

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