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SYNTHESIS OF MONOSUBSTITUTED TRIFLUOTOMETHYLATED DERIVATIVES OF 2H-THIETE, DIHYDROTHIOPHENES AND 2H-THIOPYRANES

Сергей A. Сирый, Вадим M. Тимошенко, Тимофей B. Руденко, Юрий H. Маркитанов, Эдуард Б. Русанов, Юрий Г. Шермолович
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Abstract


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.

Authors: Serhii A. Siryi, Vadim М. Тimoshenko*, Tymofii V. Rudenko, Yuriy M. Markitanov, Eduard B. Rusanov, Yuriy G. Shermolovich


Keywords


dihydrothiopyranone; keto sulfide; Ruppert–Prakash reagent; thiolactone; trifluoromethyl; vinylsulfone

Full Text: PDF (Russian) Supplementary File(s): Рисунок 1 (39KB) Supporting information (6MB)


 

 

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