Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Gas Chromatographic Investigation of Stereoisomeric Cyclotrideca-1,5,9-trienesUsing achiral phases of different polarity in capillary gas chromatography on the one hand and a chiral cyclodextrine phase on the other hand it is demonstrated, that a ring-enlargement sequence starting from (E, E, Z)-cyclododeca-1,5,9-triene yields five of the six theoretically possible isomeric cyclotrideca-1,5,9-trienes and (E, Z)-trans-bicyclo[10.1.0]trideca- 4,8-diene. With all achiral phases only three of the isomeric trienes and the bicyclic isomer were separated from each other; (E, Z, E)- and (Z, E, Z)-cyclotrideca-1,5,9-triene are eluated in only one (the fifth) peak, these isomers were separated on the cyclodextrine phase. Moreover, this chiral phase separates the enantiomers of the bicyclic isomer.
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