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Condensation of acetylacetone with formaldehyde and thiols

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Abstract

Acetylacetone reacted with formaldehyde and thiols in aqueous medium or in the presence of 0.1 equiv of sodium hydroxide to give the corresponding 3-[(alkylsulfanyl)methyl]pentane-2,4-diones which exist in solution as mixtures of diketone and enol tautomers. Four-component condensation of acetylacetone with formaldehyde, methanethiol, and sodium sulfide, depending on the reaction time, led to the formation of a mixture of 1,1-bis(methylsulfanylmethyl)propan-2-one with 1,1′-{3-[(methylsulfanyl)methyl]tetrahydro-2H-thiopyran-3,5-diyl}diethanone or with 8-methyl-5-(methylsulfanylmethyl)-3-thiabicyclo[3.3.1]non-7-en-6-one.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    L. A. Baeva, L. F. Biktasheva, A. A. Fatykhov & N. K. Lyapina

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  1. L. A. Baeva
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  2. L. F. Biktasheva
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  3. A. A. Fatykhov
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  4. N. K. Lyapina
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Correspondence to L. A. Baeva.

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Original Russian Text © L.A. Baeva, L.F. Biktasheva, A.A. Fatykhov, N.K. Lyapina, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 9, pp. 1300–1303.

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Baeva, L.A., Biktasheva, L.F., Fatykhov, A.A. et al. Condensation of acetylacetone with formaldehyde and thiols. Russ J Org Chem 49, 1283–1286 (2013). https://doi.org/10.1134/S1070428013090078

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  • DOI: https://doi.org/10.1134/S1070428013090078

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