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 language | English (US) |
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Pages (from-to) | 175-181 |
Number of pages | 7 |
Journal | Journal of Fluorine Chemistry |
Volume | 115 |
Issue number | 2 |
DOIs | |
State | Published - Jun 28 2002 |
Keywords
- Oxathiin
- Phthalimidosulfenyl chloride
- Polyfluoroalkyl ketone
- Succinimidosulfenyl chloride
- Thiin
- α-thioxoketone