Synthesis of 5,6-dihydro-2H-thiins and 2,3-dihydro-1,4-oxathiins based on 1-benzylsulfonyl-1,1-dihydropolyfluoroalkan-2-ones

S. V. Yemets, Yu P. Bandera, V. M. Timoshenko, Yu G. Shermolvich

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7 Scopus citations

Abstract

1-Benzylsulfonyl-1,1-dihydropolyfluoroalkan-2-ones react with phthalimidosulfenyl chloride or succinimidosulfenyl chloride to form the sulfenylated products on the active methylene group, 1-benzylsulfonyl-1-phthalimido(succinimido)thiopolyfluoroalkan-2-ones. Decomposition of the latter leads to formation of 1-benzylsulfonyl-1-thioxopolyfluoroalkan-2-ones. These compounds easily undergo the hetero Diels-Alder reaction with electron-rich 1,3-dienes as dienophiles and with electron-rich olefins as hetero-1,3-dienes. Polyfluoroalkyl substituted derivatives of six-membered sulfur-containing heterocycles, 5,6-dihydro-2H-thiins and 2,3-dihydro-1,4-oxathiins, are obtained as a result of these reactions.

Original languageEnglish (US)
Pages (from-to)175-181
Number of pages7
JournalJournal of Fluorine Chemistry
Volume115
Issue number2
DOIs
StatePublished - Jun 28 2002

Keywords

  • Oxathiin
  • Phthalimidosulfenyl chloride
  • Polyfluoroalkyl ketone
  • Succinimidosulfenyl chloride
  • Thiin
  • α-thioxoketone

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