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Wegert, Anita; Reinke, Helmut; Miethchen, Ralf
Carbohydrate research, 07/2004, Letnik: 339, Številka: 10Journal Article
Graphic The attempted conversion, by treatment with CsF/TBFA in MeCN, of acetylated derivatives of 2-chlorodifluoromethyl-2-deoxyhexopyranoses into their corresponding 2-trifluoromethyl derivatives was always accompanied by an elimination reaction. Thus, representative educts with the d- gluco- and d- manno-configuration gave derivatives of 2,3-dideoxy-2-trifluoromethyl- d- erythro-hex-2-enopyranose and 1,5-anhydro-2-deoxy-2-trifluoromethyl- d- arabino-hex-1-enitol, respectively. X-ray analyses are given for 1,3,4,6-tetra- O-acetyl-2-chlorodifluoromethyl-2-deoxy-α- d-mannopyranose and 4,6-di- O-acetyl-2,3-dideoxy-2-trifluoromethyl-α- d- erythro-hex-2-enopyranose.
