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Quantum Chemical Study of the Addition of Secondary Phosphine Chalcogenides to Vinyl Selenides

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Abstract

DFT quantum chemical calculations at the B3PW91/6-31G(d) level of theory have shown that the addition of secondary phosphine sulfides and phosphine selenides with alkyl, phenyl, and phenylalkyl substituents to pentyl vinyl and hexyl vinyl selenides follows a molecular mechanism against the Markovnikov rule through energetically favorable eight-membered transition state, leading to the formation of tertiary phosphine chalcogenides. Secondary phosphine selenides are more reactive than the corresponding phosphine sulfides.

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ACKNOWLEDGMENTS

Quantum chemical calculations were performed at the computational center, Kazan Branch, Interinstitutional Supercomputer Center, Russian Academy of Sciences (a branch of “Scientific Research Institute for System Analysis” Federal Scientific Center, Russian Academy of Sciences) and at the Kazan Federal University.

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 16-03-00100 a).

Author information

Authors and Affiliations

  1. Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    Ya. A. Vereshchagina & R. R. Ismagilova

  2. Kazan Branch, Joint Supercomputer Center, Russian Academy of Sciences (Branch of “Scientific Research Institute for System Analysis” Federal Research Center, Russian Academy of Sciences), 420111, Kazan, Russia

    D. V. Chachkov

  3. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    N. A. Chernysheva

Authors
  1. Ya. A. Vereshchagina
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  2. R. R. Ismagilova
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  3. D. V. Chachkov
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  4. N. A. Chernysheva
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Corresponding author

Correspondence to Ya. A. Vereshchagina.

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Vereshchagina, Y.A., Ismagilova, R.R., Chachkov, D.V. et al. Quantum Chemical Study of the Addition of Secondary Phosphine Chalcogenides to Vinyl Selenides. Russ J Org Chem 56, 1696–1701 (2020). https://doi.org/10.1134/S1070428020100048

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  • DOI: https://doi.org/10.1134/S1070428020100048

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