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Quantum chemical study of mechanisms of organic reactions: V. Addition of ethane-1,2-dithiol to 4-hydroxy-4-methylpent-2-ynenitrile

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Abstract

The mechanism of nucleophilic addition of ethane-1,2-dithiol to 4-hydroxy-4-methylpent-2-ynenitrile has been studied at the DFT B3LYP/6-311++G(d,p) level of theory. The base-catalyzed reaction involves nucleophilic attack by deprotonated ethane-1,2-dithiol on the ß-carbon atom of the nitrile with formation of intermediate Z-vinylic carbanion which undergoes intramolecular cyclization with closure of 1,3-dithiolane ring. Further transformation of 2-[2-(2-hydroxypropan-2-yl)-1,3-dithiolan-2-yl]acetonitrile to 6,6-dimethyl-7-oxo-1,4-dithiaspiro[4.4]nonan-8-imine has also been studied.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    E. A. Chirkina, A. G. Mal’kina, I. A. Ushakov & L. B. Krivdin

Authors
  1. E. A. Chirkina
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  2. A. G. Mal’kina
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  3. I. A. Ushakov
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  4. L. B. Krivdin
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Correspondence to E. A. Chirkina.

Additional information

Original Russian Text © E.A. Chirkina, A.G. Mal’kina, I.A. Ushakov, L.B. Krivdin, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1279–1289.

For communication IV, see [1].

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Chirkina, E.A., Mal’kina, A.G., Ushakov, I.A. et al. Quantum chemical study of mechanisms of organic reactions: V. Addition of ethane-1,2-dithiol to 4-hydroxy-4-methylpent-2-ynenitrile. Russ J Org Chem 52, 1267–1276 (2016). https://doi.org/10.1134/S1070428016090037

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  • DOI: https://doi.org/10.1134/S1070428016090037

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