D1(1H,1H,2H,2H-perfluorooctyl)-dibenzo-18-crown-6 A light fluorous recyclable phase transfer catalyst

series of dibenzo-18-crown-6 lariat ethers containing two C(7)H(15) (11) (CH(2))(2)C(6)F(13) (14) (CH(2))(2)C(8)F(17) (15) NHC(7)H(15) (18) and NHCH(2)C(6)F(13) (19) sidearms were prepared and the single crystal X-ray structure of cis-4 4'-di(1H 1H 2H 2H-perfluorodecyl)-dibenzo-18-crown 6 (15a) is reported The light fluorous dibenzo-18-crown-6 ether (14) has emerged as a stable and robust PTC catalyst which can be recycled efficiently by fluorous solid-phase extraction and gives better PTC catalytic activity compared to the parent non-fluorinated PTC catalyst dibenzo-18-crown-6 and the alkylated derivative (11) in aliphatic and aromatic nucleophilic substitutions (C) 2010 Elsevier B V All rights reserved