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Title of article :
Practice of fluorous biphase chemistry: convenient synthesis of novel fluorophilic ethers via a Mitsunobu reaction
Author/Authors :
Rلbai، نويسنده , , Jَzsef and Szabَ، نويسنده , , Dénes and Borbلs، نويسنده , , Eszter K and Kِvesi، نويسنده , , Istvلn and Kِvesdi، نويسنده , , Istvلn and Csلmpai، نويسنده , , Antal and Gِmِry، نويسنده , , ءgnes and Pashinnik، نويسنده , , Valeriy E and Shermolovich، نويسنده , , Yuriy G، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2002
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Abstract :
The evolution of the term fluorous is addressed first, then a concise terminology is proposed, including fluorous partition coefficient, specific fluorophilicity and fluorousness. Some examples are shown for the design of higher generation fluorophilic molecules, involving Class I to Class III ponytails. Fluorophilic ethers of the structure of ArC(CF3)2O(CH2)m(CF2)nF (m=1, n=1, 7; m=3, n=8) are obtained in high yields, when 2-aryl-1,1,1,3,3,3-hexafluoro-propanols are reacted either with trifluoroethyl- and 1H,1H-perfluorooctyl triflates (NaH/DMF, Williamson ether synthesis) or with 3-perfluorooctyl-propanol (Ph3P/EtO2CNNCO2Et/PhCF3, Mitsunobu reaction), respectively. Fluorophilic phenol- and perfluoro-tert-butyl ethers can also be prepared effectively by the latter method. In case of higher homologues (n=7, 8) product isolation can be facilitated using fluorous extraction (C6F14/CH3OH). Specific fluorophilicity values of target molecules are estimated using a 2D method and compared with experimentally determined ones.
Keywords :
Mitsunobu reaction , Specific fluorophilicity , fluorine , Perfluoroalkylmethyl triflates
Journal title :
Journal of Fluorine Chemistry
Link To Document :