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Quantum chemical study of mechanisms of organic reactions: IV. Nucleophilic addition of ethylene glycol to 4-hydroxybut-2-ynenitrile

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Abstract

A theoretical mechanism has been proposed for nucleophilic addition of ethylene glycol to 4-hydroxybut-2-ynenitrile on the basis of DFT quantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory. The reaction catalyzed by alkali involves nucleophilic attack by 2-hydroxyethoxide ion on the β-carbon atom of the acetylenic alcohol with intermediate formation of vinylic carbanion which undergoes intramolecular cyclization with closure of 1,3-dioxolane ring.

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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 & L. B. Krivdin

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

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Dedicated to Full Member of the Russian Academy of Sciences V.I. Minkin on his 80th anniversary

Original Russian Text © E.A. Chirkina, A.G. Mal’kina, L.B. Krivdin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 331–336.

For communication III, see [1].

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Chirkina, E.A., Mal’kina, A.G. & Krivdin, L.B. Quantum chemical study of mechanisms of organic reactions: IV. Nucleophilic addition of ethylene glycol to 4-hydroxybut-2-ynenitrile. Russ J Org Chem 51, 313–318 (2015). https://doi.org/10.1134/S1070428015030045

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  • DOI: https://doi.org/10.1134/S1070428015030045

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