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Chemoselective reaction of aryl azides with ethyl 3-oxo-4-(triphenylphosphor- anylidene) butanoate

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of aryl azides with ethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate has been studied under different conditions and it was found that the reaction occurs chemoselectively to form one of two possible isomers. Novel (1H-1,2,3-triazol-5-yl)acetic acids have been synthesized.

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Correspondence to M. D. Obushak.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1823-1827, December, 2009.

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Pokhodylo, N.T., Matiychuk, V.S. & Obushak, M.D. Chemoselective reaction of aryl azides with ethyl 3-oxo-4-(triphenylphosphor- anylidene) butanoate. Chem Heterocycl Comp 45, 1469–1472 (2009). https://doi.org/10.1007/s10593-010-0452-y

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  • DOI: https://doi.org/10.1007/s10593-010-0452-y

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