[Enantiomeric resolution of trans-1,2-disubstituted cyclopropane by high performance liquid chromatography].
The enantiomeric resolution of racemic mixtures of thirteen trans-1,2-disubstituted cyclopropane was achieved with HPLC by using Chiralcel OD and Chiralcel OJ as chiral stationary phase and hexane/2-propanol mixtures with different concentrations as eluent. The chromatographic parameters of these racemates on Chiralcel OD and Chiralcel OJ columns were examined. The results showed that enantiomeric resolution ability of the racemic mixtures of trans-1,2-disubstituted cyclopropane on Chiralcel OD and Chiralcel OJ was strongly dependent on the site and the property of substituents on the benzene cycle. On the other hand, some racemated of trans-1,2-disubstituted cyclopropane with aliphatic group were also separated on the columns. The results showed that the chiral recognition process was the sum of all the possible chiral interaction (the dipole-dipole, hydrogen bond-hydrogen bond and pi-pi interactions) between the chiral stationary phase and trans-1,2-disubstituted cyclopropane. This method has been applied to identify the optical purity of trans-1,2-disubstituted cyclopropane.
Xia
L
L
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032.
Zhou
S
S
Tang
M
M
Lin
L
L
Deng
M
M
D002851:Chromatography, High Pressure Liquid; D003511:Cyclohexanols / Q000032:analysis / Q000737:chemistry; D003521:Cyclopropanes / Q000032:analysis / Q000737:chemistry*; D013237:Stereoisomerism
D003511:Cyclohexanols; D003521:Cyclopropanes; C417982:1,2-dimethylcyclopropane; C064619:1,2-cyclohexanediol; C030797:cyclopropane