Gas chromatographic behaviour of isomeric tricyclo[10.4.0.04,9]hexadecanes

Summary Using achiral stationary phases of different polarity in capillary gas chromatography it is demonstrated that the hydration of 1,2–5,6-dibenzocycloocta-1,5-diene yields five isomers of the tricyclo10.4.0.0^4,9]hexadecanes. With highly polar stationary phases all isomers of the tricyclic hexadecanes and the semihydrated products in the mixture were also separated from each other. The chiral isomers were separated on cyclodextrin stationary phase. Moreover, with columns of achiral and chiral phases coupled in series, in a double oven gas chromatograph, it was possible to estimate the configuration of the isomers. The separation of diastereomers on chiral stationary phases is a useful means for structural assignment of isomeric compounds.Dedicated to Professor Leslie S. Ettre on the occasion of his 70th birthday.