SummaryNew p-and y-cyclodextrin derivatives, selectively substituted with n-pentyl and methyl groups, e.g. heptakis(2,6-di-Omethyl-3-O-pentyl)-~-cyclodextrin, octakis(2-O-methyl-3,6-di-0-penty1)-y-cyclodextrin, and octakis(2,6-di-O-methyl-3-0-penty1)-y-cyclodextrin, have been prepared from specifically protected intermediates.The new cyclodextrin derivatives exhibit unique enantioselectivity towards important chiral constituents of essential oils. The enantiomers of lavandulol, abisabolol, nerolidol, and other terpenoid alcohols could be resolved and their presence in different essential oils could be proved. Methyl jasmonate and epi-methyl jasmonate could, in addition, be detected in jasmine concrete by two-dimensional gas chromatography. The enantiomers of the macrocyclic ketone muscone have been separated for the first time.

SummaryA number of sesquiterpene hydrocarbons commonly occurring in essential oils has been prepared as racemic mixtures by chemical synthesis. Preparative gas chromatography with selectively per-O alkylated cyclodextrins has been employed for the isolation of enantiomeric mixtures or pure enantiomers from the essential oils of higher plants and liverworts (Hepaticae). The enantiomers of a-curcumene, a-and P-bisabolene, p-elemene, 6-elemene, a-copaene, Bcadinene, cis-and trans-calamenene, and bicyclogermacrene could be resolved by enantioselective gas chromatography on capillary columns coated with cyclodextrin derivatives. The enantiomeric composition of these sesquiterpene hydrocarbons in various essential oils was determined.

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SummaryThe enantiomers of the polychlorinated polycyclic xenobiotics heptachlor, cis-and trans-chlordane, cis-and trans-heptachlorepoxide, oxychlordane, and bromocyclen have been resolved by gas chromatography with selectively substituted cyclodextrins. The order of elution of these compounds and of a-hexachlorocyclohexane (a-HCH) was determined by comparison with enantiomerically enriched reference compounds obtained by preparative enantioselective gas chromatography.A separation of the eight stereoisomers of the pyrethroid insecticide allethrin into seven peaks was achieved. Both trans-diastereomers were separated into their enantiomers and the order of elution could be determined by comparison with commercially available (S)-bioallethrin and trans-bioallethrin. Also one cis-diastereomer was separated, wheras the other cis-isomer could not be resolved. In addition 15 out of 19 stable atropisomeric polychlorinated biphenyls with 5, 6 and 7 chlorine substituents, some chiral organophosphorus pesticides, including acephate and malaoxon and the herbicide bromoacil were separated.