Strategy and design in fluorous phase immobilization:­a systematic study of the effect of ‘pony tails’ (CH 2 ) 3 (CF 2 )   n −1 CF 3  on the partition coefficients of ­benzenoid compounds | Zendy

Rocaboy Christian | Zendy; Rutherford Drew | Zendy; Bennett Byron L. | Zendy; Gladysz J. A. | Zendy

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Strategy and design in fluorous phase immobilization:a systematic study of the effect of ‘pony tails’ (CH 2 ) 3 (CF 2 ) n −1 CF 3 on the partition coefficients of benzenoid compounds

Author(s) -

Rocaboy Christian,

Rutherford Drew,

Bennett Byron L.,

Gladysz J. A.

Publication year - 2000

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/1099-1395(200010)13:10<596::aid-poc284>3.0.co;2-m

Subject(s) - alkylbenzenes , chemistry , toluene , partition coefficient , yield (engineering) , organic chemistry , reagent , catalysis , phase (matter) , pony , combinatorial chemistry , thermodynamics , history , physics , archaeology

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 ) n −1 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. Copyright © 2000 John Wiley & Sons, Ltd.

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