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
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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. Copyright © 2000 John Wiley & Sons, Ltd.
author list (cited authors)
Rocaboy, C., Rutherford, D., Bennett, B. L., & Gladysz, J. A.