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Quantum-chemical study of mechanisms of reaction between 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde with 2-mercaptoethanol

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Abstract

By quantum-chemical method MP2/6-311+G**//B3LYP/6-31+G** competing reaction channels were studied of the formation of pyrazolyl-1,3-oxathiolane and/or bis(2-hydroxyethyl)dithioacetal from 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde and 2-mercaptoethanol. The kinetically controlled formation of bis(2-hydroxyethyl) dithioacetal is governed by the concentration in the reaction mixture of 2-mercaptoethanol dimers. The reaction by stages of 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde with the molecules of mercaptoethanol results in the prevailing formation of 2-(pyrazol-4-yl)-1,3-oxathiolane structures.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    V. A. Shagun, A. A. Shatrova, L. K. Papernaya & G. G. Levkovskaya

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  1. V. A. Shagun
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  2. A. A. Shatrova
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  3. L. K. Papernaya
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  4. G. G. Levkovskaya
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Correspondence to L. K. Papernaya.

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Original English Text © V.A. Shagun, A.A. Shatrova, L.K. Papernaya, G.G. Levkovskaya, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 2, pp. 284–289.

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Shagun, V.A., Shatrova, A.A., Papernaya, L.K. et al. Quantum-chemical study of mechanisms of reaction between 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde with 2-mercaptoethanol. Russ J Org Chem 49, 276–282 (2013). https://doi.org/10.1134/S1070428013020164

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  • DOI: https://doi.org/10.1134/S1070428013020164

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