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Radical Intermediates in Reactions of Mixed Phosphonium–Iodonium Ylides

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Abstract

The active intermediates generated in the photolysis of phosphonium–iodonium ylides and their reaction with acetylenes have been studied with electron and nuclear magnetic resonance spectroscopy. The radical mechanism of the ylides decomposition and of the interaction with acetylenes has been established using a stable nitroxyl radical. The radical products of these reactions have been monitored for the first time by EPR, and their spectroscopic parameters were determined. The chemical structure of the active intermediates of the reactions under study has been proposed.

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ACKNOWLEDGMENTS

Spectral measurements by the EPR and 31P NMR spectroscopy were carried out in the Center of Shared Facilities of IBCP RAS “New Materials and Technologies”.

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Correspondence to T. D. Nekipelova.

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This study was supported by the RF State Program for IBCP RAS, project no. 1201253303.

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Translated by T. Nekipelova

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Nekipelova, T.D., Motyakin, M.V., Kasparov, V.V. et al. Radical Intermediates in Reactions of Mixed Phosphonium–Iodonium Ylides. Russ. J. Phys. Chem. B 13, 907–914 (2019). https://doi.org/10.1134/S1990793119060265

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Keywords:

  • phosphonium-iodonium ylides
  • photolysis
  • reaction with acetylenes
  • radical intermediates
  • EPR
  • 31P NMR