SYNTHESIS OF MONOSUBSTITUTED TRIFLUOTOMETHYLATED DERIVATIVES OF 2<i>H</i>-THIETE, DIHYDROTHIOPHENES AND 2<i>H</i>-THIOPYRANES

Authors

  • Сергей A. Сирый Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094
  • Вадим M. Тимошенко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094
  • Тимофей B. Руденко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094 2Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094
  • Юрий H. Маркитанов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094
  • Эдуард Б. Русанов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094
  • Юрий Г. Шермолович Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094

DOI:

https://doi.org/10.1007/6529

Keywords:

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

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

Author Biography

Вадим M. Тимошенко, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094

Laboratory of organosulfur compounds

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Published

2022-03-09

Issue

Vol. 58 No. 2/3 (2022)

Section

Original Papers