Strategy and design in fluorous phase immobilization: a systematic study of the effect of 'pony tails' (CH2)(3)(CF2)(n-1)CF3 on the partition coefficients of benzenoid compounds

Fluorous solvents commonly exhibit temperature-dependent miscibilities with organic solvents. Thus, catalysts and reagents that have high affinities f or fluorous solvents can be used in protocols that combine the advantages o f one-phase chemistry (higher temperature) and biphase product separation ( lower temperature). The high-yield conversion of benzaldehydes (via Wittig and hydrogenation reactions) to alkylbenzenes with one to three 'pony tails ' (CH2)(3)(CF2)(n-1)CF3 (n = 6, 8, 10) is described. The toluene-CF3C6F11 p artition coefficients show that three pony tails are necessary to achieve a high degree of fluorous phase immobilization. Copyright (C) 2000 John Wile y & Sons, Ltd.