Journal of the American Chemical Society p. 6486 - 6492 (1987)
Update date:2022-08-05
Topics:
Klein, Michael
Wingen, Ute
Buss, Volker
UV and CD spectra of eight β-cyclocitral Schiff bases rendered chiral by virtue of an asymmetrically substituted imine part have been measured and rationalized on the basis of force-field (MMP2) and quantum-mechanical (CNDO) calculations.They show the compounds to exist as a temperature- and solvent-dependent mixture of highly twisted s-cis and close to planar, but less stable s-trans conformers.Both ??* and n?* absorptions are unambigously assigned, the former in the UV spectra, and the latter in the CD spectra; however, only the sign of the n?* band correlates with the absolute conformation of the diene, being plus for M and minus for P helicity.
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