Condensation of 3,5-Dialkyltetrahydro-4H-thiopyran-4-ones with Formaldehyde

The reaction of 3,5-dimethyl- and 5-methyl-3-(2-propyl)tetrahydro-4 H -thiopyran-4-ones with formaldehyde without or in the presence of 0.1–0.5 equiv. sodium hydroxide produces 3,5-dialkyl-3-(hydroxymethyl)tetrahydro-4 H -thiopyran-4-ones. 3,5-Dimethyltetrahydro-4 H -thiopyran-4-one converted into 3...

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Published inRussian journal of general chemistry Vol. 92; no. 9; pp. 1677 - 1685
Main Authors Baeva, L. A., Biktasheva, L. F., Gataullin, R. R., Fatykhov, A. A.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.09.2022
Springer Nature
Springer
Springer Nature B.V
Subjects
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Formaldehyde
Hydroxides
Physical Sciences
Science & Technology
Sodium hydroxide
tetrahydro-4
thiopyran-4-one
aldol condensation reaction
formaldehyde
Cannizzaro reaction
tetrahydro-4H-thiopyran-4-one
INHIBITORS
DERIVATIVES
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Summary:The reaction of 3,5-dimethyl- and 5-methyl-3-(2-propyl)tetrahydro-4 H -thiopyran-4-ones with formaldehyde without or in the presence of 0.1–0.5 equiv. sodium hydroxide produces 3,5-dialkyl-3-(hydroxymethyl)tetrahydro-4 H -thiopyran-4-ones. 3,5-Dimethyltetrahydro-4 H -thiopyran-4-one converted into 3,5-bis(hydroxymethyl)tetrahydro-2 H -thiopyran-4-ol when the amount of base to 1 equiv increase. Under similar conditions 5-methyl-3-(2-propyl)tetrahydro-4 H -thiopyran-4-one form 3-hydroxymethyltetrahydro-2 H -thiopyran-4-ol, which cyclization to 7-oxa-3-thiabicyclo[4.2.0]octane.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363222090092