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
✍ Scribed by Christian Rocaboy; Drew Rutherford; Byron L. Bennett; J. A. Gladysz
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 117 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0894-3230
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✦ Synopsis
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' (CH 2 ) 3 (CF 2 ) nÀ1 CF 3 (n = 6, 8, 10) is described. The toluene-CF 3 C 6 F 11 partition coefficients show that three pony tails are necessary to achieve a high degree of fluorous phase immobilization.