Synthesis and some chemical properties of the 6-arylsulfonyl-6-polyfluoroalkanoyl-5,6-dihydro-2H-thiins - New fluorine-containing ketones

Yu P. Bandera, Sergiy V Yemets, V. M. Timoshenko, A. M. Nesterenko, A. N. Chernega, Yu G. Shermolovich

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

1,1-Dihydro-1-tolylsulfonyl polyfluoroalkan-2-ones react with phthalimidosulfenyl chloride to form sulfenylated products on the active methylene group, 1-phthalimidothio-1-tolylsulfonyl polyfluoroalkan-2-ones. Decomposition of the latter leads to formation of 1-thioxo-1-tolylsulfonyl polyfluoroalkan-2-ones. These compounds undergo easily the hetero Diels-Alder reaction with electron-rich 1,3-dienes as dienophiles to give polyfluoroalkanoyl substituted derivatives of 5,6-dihydro-2H-thiins. 6-Arylsulfonyl-6-polyfluoroalkanoyl-5,6-dihydro-2H-thiins obtained react with alkali to give 5,6-dihydro-6- p -tolylsulfonyl-2H-thiins and with methanol to give 2-polyfluoroalkanoyl-6H-thiins.

Original languageEnglish (US)
Pages (from-to)197-205
Number of pages9
JournalJournal of Fluorine Chemistry
Volume123
Issue number2
DOIs
StatePublished - Oct 1 2003
Externally publishedYes

Keywords

  • Cycloaddition
  • Polyfluoroalkyl ketone
  • Thiin
  • α-Thioxoketone

Fingerprint Dive into the research topics of 'Synthesis and some chemical properties of the 6-arylsulfonyl-6-polyfluoroalkanoyl-5,6-dihydro-2H-thiins - New fluorine-containing ketones'. Together they form a unique fingerprint.

Cite this