Optical rotatory dispersion and circular dichroism of diastereoisomers. I. The ephedrines and chloramphenicols

Authors:
  • LML. A. Mitscher
    L. A. Mitscher
  • FKF. Kautz
    F. Kautz
  • JLJ. LaPidus
    J. LaPidus
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Abstract
Optical rotatory dispersion (o.r.d.) and circular dichroism measurements are reported for all four diastereoisomers in both the ephedrine and chloramphenicol series. The Cotton effect associated with the 1Lb absorption band is a reliable guide to absolute configuration in both series whereas the 1La band is not. Circular dichroism measurements are preferred as the 1La band dominates the o.r.d. curves to such an extent that erroneous assignment is quite possible. An attempt to relate the sign and intensity of the 1Lb Cotton effect with rotamer population failed due to lack of apparent correlation.