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Synthesis of Monosubstituted Trifluoromethylated Derivatives of 2H-thiete, Dihydrothiophenes, and 2H-thiopyrans

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Chemistry of Heterocyclic Compounds Aims and scope

Cyclic keto sulfides (thietan-3-one, tetrahydrothiophen-3-one, γ-thiobutyrolactone, δ-thiovalerolactone, thiopyran-3-one, and thiopyran-4-one) react with trifluoromethyltrimethylsilane (Ruppert–Prakash reagent) to afford trifluoromethyl-substituted hydroxysulfides which form monotrifluoromethyl-substituted cyclic unsaturated sulfones via successive oxidation and dehydration reactions. It was shown that the double bond in the obtained compounds is active toward nucleophilic reagents such as amino compounds and 1,3-dipoles.

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Correspondence to Vadim М. Тimoshenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(2/3), 106–115

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Siryi, S.A., Тimoshenko, V.М., Rudenko, T.V. et al. Synthesis of Monosubstituted Trifluoromethylated Derivatives of 2H-thiete, Dihydrothiophenes, and 2H-thiopyrans. Chem Heterocycl Comp 58, 106–115 (2022). https://doi.org/10.1007/s10593-022-03063-0

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