Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5268256 | Tetrahedron Letters | 2010 | 4 Pages |
Abstract
2-Polyfluoroalkylthiopyrylium salts have been synthesized by oxidative aromatization of 2-polyfluoroalkyl-2H-thiopyrans with triphenylmethane tetrafluoroborate. Nucleophilic addition of methanol, sodium azide, or urea to 2-trifluoromethylthiopyrylium tetrafluoroborate in a basic medium proceeds at the α-position to give the corresponding 2-substituted 6-trifluoromethyl-2H-thiopyrans whereas imidazoles, fluorine-containing 1,2,3-triazole, potassium thiolacetate, and sodium nitromethane afford mixtures of 2H- and 4H-thiopyrans. cis-Dihydroxylation of 6-trifluoromethyl-2-methoxy-2H-thiopyran affords the fluorine-containing thiohexenopyranoside derivative 8.
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Authors
Sergiy A. Siry, Vadim M. Timoshenko,