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Condensation of formyl-substituted indoline spiropyrans with 3H-indolium salts: specific features

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Abstract

A condensation reaction between formyl-containing spiropyrans and iodides of 1,2,3,3-tetramethyl-3H-indolium derivatives was studied. The reaction results in a mixture of products with a strong predominance of one of them irrespective of the structure of the starting compounds. The structures of the compounds formed during the reaction were determined based on the NMR, IR, and mass spectroscopy data. The dependence of the yield of the major reaction product on the structure of the starting compounds was studied. The prerequisites for the observed reaction pathway were established and the reaction mechanism was proposed using the results of quantum-chemical calculations based on analysis of the molecular electrostatic potential and the dual descriptor of reactivity.

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    A. S. Kozlenko, A. D. Pugachev, I. V. Ozhogin, G. S. Borodkin, V. I. Minkin, V. V. Bykusov & B. S. Lukyanov

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. V. Tkachev

Authors
  1. A. S. Kozlenko
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  2. A. D. Pugachev
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  3. I. V. Ozhogin
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  4. G. S. Borodkin
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  5. V. I. Minkin
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  6. V. V. Bykusov
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  7. V. V. Tkachev
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  8. B. S. Lukyanov
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Corresponding author

Correspondence to A. S. Kozlenko.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation within the framework of the State Assignment to the South Federal University (Reg. No. 0852-2020-00-19, synthesis of compound, structure determination by NMR spectroscopy, and quantum chemical modeling) and within the framework of the State Assignment to the Institute of Problems of Chemical Physics, Russian Academy of Sciences (Reg. No. AAAA-A19-119092390076-7, V. V. Tkachev, a vibrational spectroscopy study).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 979–989, April, 2023.

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Kozlenko, A.S., Pugachev, A.D., Ozhogin, I.V. et al. Condensation of formyl-substituted indoline spiropyrans with 3H-indolium salts: specific features. Russ Chem Bull 72, 979–989 (2023). https://doi.org/10.1007/s11172-023-3863-9

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  • DOI: https://doi.org/10.1007/s11172-023-3863-9

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