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Cyanoacetylene and Its Derivatives. 29. New Data on Synthesis and Properties of Substituted 1,3-Oxathiolan-2-ones

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Abstract

We have determined the conditions for carrying out the reaction of 4-alkyl-4-hydroxy-2-alkynonitriles containing bulky or spirocyclic substituents with the KSCN-KHSO4 system, leading to 5,5-dialkyl-4-cyanomethylene-1,3-oxathiolan-2-ones in quantitative yield (for this, we had to increase the reaction time and use a 10-fold excess of the hydrothiocyanating system compared with the known conditions). 5,5-Dimethyl-4-cyanomethyl-1,3-oxathiolan-2-one reacts with methanol in the presence of triethylamine (20±2°C), forming 2-cyanomethyl-4-cyanomethylene-2-[(1-methoxycarbonyloxyethyl-1-methyl)]-5,5-dimethyl-1,3-dithiolane (yield 90%).

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Authors and Affiliations

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

    I. A. Dorofeev, A. G. Mal'kina & B. A. Trofimov

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  1. I. A. Dorofeev
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  2. A. G. Mal'kina
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  3. B. A. Trofimov
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Dorofeev, I.A., Mal'kina, A.G. & Trofimov, B.A. Cyanoacetylene and Its Derivatives. 29. New Data on Synthesis and Properties of Substituted 1,3-Oxathiolan-2-ones. Chemistry of Heterocyclic Compounds 37, 903–906 (2001). https://doi.org/10.1023/A:1012416028013

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