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Synthesis of 1,2-diols ethers, condensation products of glyoxal with nitrogen-containing nucleophiles: I. Reaction of cyclic sulfites with primary alcohols and glycols

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Abstract

In reactions of 4,5-diacetoxy-2-(dinitromethylene)imidazolidine, 4,5-diacetoxy-2-nitriminoimidazolidine, and 1,2-diacetoxy-1,2-bis(chloroacetylamino)ethane with thionyl chloride at room temperature the corresponding cyclic sulfites were obtained. Treating the sulfites with methanol, ethanol, and 2-chloroethanol at room temperature we prepared acyclic ethers in 80–90% yields. Similarly cyclic ethers were synthesized from ethylene glycol and 1,3-propanediol in 50–60% yields.

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Authors and Affiliations

  1. St. Petersburg State Technological Institute, St. Petersburg, 190013, Russia

    E. V. Sizova, V. V. Sizov & I. V. Tselinskii

Authors
  1. E. V. Sizova
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  2. V. V. Sizov
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  3. I. V. Tselinskii
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Correspondence to V. V. Sizov.

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Dedicated to the Full Member of the Russian Academy of Sciences V.A.Tartakovsky on occasion of his 75th birthday

Original Russian Text © E.V. Sizova, V.V. Sizov, I.V. Tselinskii, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 8, pp. 1217–1221.

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Sizova, E.V., Sizov, V.V. & Tselinskii, I.V. Synthesis of 1,2-diols ethers, condensation products of glyoxal with nitrogen-containing nucleophiles: I. Reaction of cyclic sulfites with primary alcohols and glycols. Russ J Org Chem 43, 1213–1217 (2007). https://doi.org/10.1134/S1070428007080222

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  • DOI: https://doi.org/10.1134/S1070428007080222

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