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Conversion of a racemate into a single enantiomer in one step by chiral liquid chromatography: Studies with rac ‐2,2′‐diiodobiphenyl
Author(s) -
Wolf Christian,
Köunig Wilfried A.,
Roussel Christian
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070809
Subject(s) - chemistry , racemization , enantiomer , elution , chromatography , biphenyl , chiral column chromatography , lability , microcrystalline , high performance liquid chromatography , stereochemistry , organic chemistry , crystallography
The enantiomers of rac ‐2,2′‐diiodobiphenyl were separated by liquid chromatography on microcrystalline triacetylcellulose. The conformational lability, a large separation factor α, and a suitable capacity factor k ′(+) of this biphenyl allowed us to convert the racemate into 90% of enantiomerically pure (‐)‐2,2′‐diiodobiphenyl and 10% of pure (+)‐2,2′‐diiodobiphenyl, respectively, by a series of in situ racemization‐elution cycles. The much better retained (+)‐enantiomer was racemized on the chromatographic column at 50°C after the less retained (‐)‐enantiomer has already been eluted at 8°C. © 1995 Wiley‐Liss, Inc.