ENANTIOMER SEPARATION OF ALPHA-CAMPHOLENE AND FENCHOLENE DERIVATIVES BY CAPILLARY GAS-CHROMATOGRAPHY ON PERMETHYLATED CYCLODEXTRIN PHASES .2. COMPOUNDS SEPARABLE WITH COUPLED TECHNIQUES

Odoriferous substances, such as sandal and woody notes of the alpha-campholene and fencholene type with two and more stereogenic centres, were analyzed by capillary gas chromatography on permethylated cyclodextrins dissolved in polysiloxanes. From enantiomer-enriched alpha-pinene compounds, received as non-racemic mixtures, the theoretically possible number of stereoisomers were determined after the introduction of additional stereogenic centres. The derivatives with two stereogenic centres were separated on single columns. In the case of substances with three stereogenic centres a serial coupling of non-chiral and chiral columns partially connected with a mass selective detector was necessary for the separation and reliable identification. For optimizing the selectivity of the serially coupled system the principle of selectivity tuning was used. This discussion also deals with the retention behaviour and the factors influencing the enantiomer separation of the alpha-campholene and fencholene compounds.