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A Simple and Convenient Synthesis of a Multifunctional Spin Probe, Phosphonate Derivative of a Persistent Radical of the Triarylmethyl Series

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Abstract

The reaction of tris(8-carboxy-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl)methanol, diamagnetic precursor of Finland trityl radical} with trifluoroacetic acid gave the corresponding triarylmethyl cation. Nucleophilic quenching of this cation with triethyl phosphite generated trityl radical containing a diethyl phosphonate moiety, and hydrolysis of the latter to phosphonic acid afforded a multifunctional oxygen- and pH-sensitive spin probe.

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ACKNOWLEDGMENTS

The authors thank the Joint Chemical Service Center (Siberian Branch, Russian Academy of Sciences) for performing the spectral and analytical measurements.

Funding

This study was financially supported in the framework of state assignment to the Novosibirsk Institute of Organic Chemistry (Siberian Branch, Russian Academy of Sciences; V.M. Tormyshev) and by the Ministry of Science and Higher Education of the Russian Federation (project no. 14.W03.31.0034; other authors).

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    O. Yu. Rogozhnikova, D. V. Trukhin, N. B. Asanbaeva & V. M. Tormyshev

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  1. O. Yu. Rogozhnikova
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  2. D. V. Trukhin
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  3. N. B. Asanbaeva
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  4. V. M. Tormyshev
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Corresponding author

Correspondence to D. V. Trukhin.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 6, pp. 820–831 https://doi.org/10.31857/S0514749221060045.

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Rogozhnikova, O.Y., Trukhin, D.V., Asanbaeva, N.B. et al. A Simple and Convenient Synthesis of a Multifunctional Spin Probe, Phosphonate Derivative of a Persistent Radical of the Triarylmethyl Series. Russ J Org Chem 57, 905–913 (2021). https://doi.org/10.1134/S107042802106004X

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