Strategy and design in fluorous phase immobilization:�a systematic study of the effect of ?pony tails? (CH2)3(CF2)n?1CF3 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 for fluorous solvents can be used in protocols that combine the advantages of 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−1CF3 (n = 6, 8, 10) is described. The toluene–CF3C6F11 partition coefficients show that three pony tails are necessary to achieve a high degree of fluorous phase immobilization.