200112-75-0Relevant articles and documents
Syntheses of fluorous quaternary ammonium salts and their application as phase transfer catalysts for halide substitution reactions in extremely nonpolar fluorous solvents
Mandal, Debaprasad,Gladysz, John A.
, p. 1070 - 1077 (2010)
Perfluoromethyldecalin solutions of the fluorous alkyl halides Rf8(CH2)mX (m=2, 3; X=Cl, I) are inert toward aqueous NaCl, KI, KCN, and NaOAc. However, substitution occurs at 100 °C in the presence of 10 mol % of the fluorous ammonium salts (Rf8(CH2)2)(Rf8(CH2)5)3N+ I- (1) or (Rf8(CH2)3)4N+ Br- (2) (10 mol %), which are fully or partially soluble in perfluoromethyldecalin under these conditions. Stoichiometric reactions of (a) 1 and Rf8(CH2)3Br, and (b) 2 and Rf8(CH2)2I are conducted in perfluoromethyldecalin at 100 °C, and yield the same Rf8(CH2)mI/Rf8(CH2)mBr equilibrium ratio (60-65:40-35). This shows that ionic displacements can take place in extremely nonpolar fluorous phases, and suggests a classical phase transfer mechanism for the catalyzed reactions. Interestingly, the non-fluorous ammonium salt mixture CH3(CH3(CH2)m)3N+ Cl- (3, Aliquat 336; m=2:1 7/9) also catalyzes halide substitutions, but under triphasic conditions with 3 suspended between the lower fluorous and upper aqueous layers. NMR experiments establish very low solubilities in both phases, suggesting interfacial catalysis.
Br?nsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water
Shen, Wei,Wang, Li-Min,Tian, He,Tang, Jun,Yu, Jian-jun
body text, p. 522 - 527 (2009/11/30)
One-pot three-component synthesis of 1,8-dioxo-9,10-diaryl-decahydroacridines in water was efficiently realized in the presence of the Br?nsted acidic imidazolium salts containing perfluoroalkyl tails in good yields. The method provided several advantages such as low catalyst loading; recycle of the catalyst and simple work procedure.
Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols
Kojima, Masaru,Nakamura, Yutaka,Ishikawa, Takuma,Takeuchi, Seiji
, p. 6309 - 6314 (2007/10/03)
N,N-Bis(perfluoroalkyl)thiocarbamoyl chlorides (FDMTC-Cls) were synthesized as reagent for the protection of alcohols. Using the crystalline FDMTC-Cls, the FDMTC groups were introduced into the alcohol molecules in excellent yields in the presence of sodium hydride in THF at room temperature. The products were separated from the excess alcohols by solid-phase extraction with a fluorous reverse-phase silica gel column (Fluorous Solid Phase Extraction; FSPE). The FDMTC groups were readily removed by oxidation with m-chloroperbenzoic acid (m-CPBA) and subsequent hydrolysis with KHCO3.