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A novel structural type of conformationally fixed, mixed phosphonium-iodonium ylides based on phenoxaphosphinine

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Abstract

A synthetic approach to a novel type of phosphonium and mixed phosphonium-iodonium ylides containing a conformationally fixed phosphonium fragment is developed. New representatives of these families of chemical compounds based on cyclic phenoxaphosphinine were synthesized. One compound was structurally characterized by single-crystal X-ray diffraction. Based on the 1H NMR data, one can state that phosphonium ylide exists in solution in the form of two geometric isomers even at room temperature. This is indicative of pronounced double-bond character of the bond between the ylide carbon atom and the stabilizing carbomethoxy group.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    A. S. Nenashev, D. S. Vinogradov, A. V. Mironov & T. A. Podrugina

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  1. A. S. Nenashev
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  2. D. S. Vinogradov
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  3. A. V. Mironov
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  4. T. A. Podrugina
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Correspondence to A. S. Nenashev.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 18-33-01039).

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Nenashev, A.S., Vinogradov, D.S., Mironov, A.V. et al. A novel structural type of conformationally fixed, mixed phosphonium-iodonium ylides based on phenoxaphosphinine. Russ Chem Bull 69, 2333–2339 (2020). https://doi.org/10.1007/s11172-020-3034-x

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  • DOI: https://doi.org/10.1007/s11172-020-3034-x

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