ISSN:
0899-0042
Keywords:
cellulose triacetate
;
tribenzoylcellulose
;
methylbenzoylcellulose
;
chiral phase
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2,2,2-Trifluoro-1-(9-anthryl)ethanol (TFAE) has now been widely used as a powerful chiral solvating agent for NMR spectroscopy. In connection with the development of a new general synthesis of halogenoalkylalkanols, starting from the corresponding ketone or aldehyde, we synthesized some halogenoalkyl-1-(9-anthryl)methanol derivatives liable to work as chiral solvating agents. The racemic anthryl derivatives were preparatively resolved into their corresponding enantiomers by chromatography on triacetyl cellulose (CTA I) or on meta-methylbenzoyl cellulose beads as chiral stationary phases. Their effectiveness as chiral solvating agents was measured as the magnitude of the splitting induced in the 1H-NMR spectra of 1-phenylethylamine and of (1-phenylethyl)methyl ether in comparison with splitting caused by TFAE. While TFAE induced the largest splitting for 1-phenylethylamine, 2,2,3,3,3-pentafluoro-1-(9-anthryl)propanol 2 was more effective in the case of (1-phenylethyl)methyl ether, pointing out that depending on the substrate, other derivatives of the TFAE type can be very useful as chiral solvating agents.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530030307
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