ISSN:
1434-4475
Keywords:
Keywords. Spiro[cyclohexadiene-dihydroacridines]; Enantiomers; Enantioselective liquid chromatography; Thermal racemization.
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary. The enantiomers of substituted spiro[cyclohexadiene-dihydroacridines] were separated by enantioselective liquid chromatography with the sorbent/solvent systems triacetylcellulose/methanol, tris-(3,5-dimethylphenylcarbamoyl)-cellulose/silica gel (Chiralcel ODTM)/n-heptane/2-propanol, and (+)-poly-(trityl methacrylate)/silica gel/n-heptane/2-propanol. Interconversion barriers of the enantiomers were determined for a series of derivatives by thermal racemization. Electrocyclic ring opening/ring closure in terms of the Woodward-Hoffmann rules is discussed for the enantiomerization mechanism; the interconversion of the enantiomers by enolization is ruled out by deuterium exchange experiments.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/s007060070041
