Condensation of acetylacetone with formaldehyde and thiols |
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Authors: | L. A. Baeva L. F. Biktasheva A. A. Fatykhov N. K. Lyapina |
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Affiliation: | 1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia
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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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