An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)(2)
Само за регистроване кориснике
2005
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Reactions of commercial fluorous alkyl iodides RfnI (1-R-fn; R-fn = CF3(CF2)(n-1); n = 7, 8, 10, 12) with 80% H2O2 and trifluoroacetic anhydride give RfnI(OCOCF3)(2) (2-R-fn; 89-97%). These rapidly oxidize 1,4-hydroquinones in methanol. Subsequent additions of CF3C6F11 or FC-72 give liquid/liquid biphase systems. The product quinones are generally isolated in gt = 95% yields from the methanol phases, and 1-R-fn in gt = 95% yields from the fluorous phases. Alternatively, the very low solubilities of 1-R-f10 in 10:1 v/v methanol : water or 1-R-f12 in methanol allow efficient recovery via solid/liquid phase separations without recourse to fluorous solvents. The recovered 1-R-fn may be reoxidized to 2-R-fn and reused.
Извор:
Green Chemistry, 2005, 7, 12, 833-836Издавач:
- Royal Soc Chemistry, Cambridge
DOI: 10.1039/b511951k
ISSN: 1463-9262
WoS: 000233361900006
Scopus: 2-s2.0-29144499129
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Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Tešević, Vele AU - Gladysz, JA PY - 2005 UR - https://cherry.chem.bg.ac.rs/handle/123456789/740 AB - Reactions of commercial fluorous alkyl iodides RfnI (1-R-fn; R-fn = CF3(CF2)(n-1); n = 7, 8, 10, 12) with 80% H2O2 and trifluoroacetic anhydride give RfnI(OCOCF3)(2) (2-R-fn; 89-97%). These rapidly oxidize 1,4-hydroquinones in methanol. Subsequent additions of CF3C6F11 or FC-72 give liquid/liquid biphase systems. The product quinones are generally isolated in gt = 95% yields from the methanol phases, and 1-R-fn in gt = 95% yields from the fluorous phases. Alternatively, the very low solubilities of 1-R-f10 in 10:1 v/v methanol : water or 1-R-f12 in methanol allow efficient recovery via solid/liquid phase separations without recourse to fluorous solvents. The recovered 1-R-fn may be reoxidized to 2-R-fn and reused. PB - Royal Soc Chemistry, Cambridge T2 - Green Chemistry T1 - An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)(2) VL - 7 IS - 12 SP - 833 EP - 836 DO - 10.1039/b511951k ER -
@article{ author = "Tešević, Vele and Gladysz, JA", year = "2005", abstract = "Reactions of commercial fluorous alkyl iodides RfnI (1-R-fn; R-fn = CF3(CF2)(n-1); n = 7, 8, 10, 12) with 80% H2O2 and trifluoroacetic anhydride give RfnI(OCOCF3)(2) (2-R-fn; 89-97%). These rapidly oxidize 1,4-hydroquinones in methanol. Subsequent additions of CF3C6F11 or FC-72 give liquid/liquid biphase systems. The product quinones are generally isolated in gt = 95% yields from the methanol phases, and 1-R-fn in gt = 95% yields from the fluorous phases. Alternatively, the very low solubilities of 1-R-f10 in 10:1 v/v methanol : water or 1-R-f12 in methanol allow efficient recovery via solid/liquid phase separations without recourse to fluorous solvents. The recovered 1-R-fn may be reoxidized to 2-R-fn and reused.", publisher = "Royal Soc Chemistry, Cambridge", journal = "Green Chemistry", title = "An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)(2)", volume = "7", number = "12", pages = "833-836", doi = "10.1039/b511951k" }
Tešević, V.,& Gladysz, J.. (2005). An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)(2). in Green Chemistry Royal Soc Chemistry, Cambridge., 7(12), 833-836. https://doi.org/10.1039/b511951k
Tešević V, Gladysz J. An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)(2). in Green Chemistry. 2005;7(12):833-836. doi:10.1039/b511951k .
Tešević, Vele, Gladysz, JA, "An easily accessed class of recyclable hypervalent iodide reagents for functional group oxidations: bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)(2)" in Green Chemistry, 7, no. 12 (2005):833-836, https://doi.org/10.1039/b511951k . .