Gas Chromatography-Mass Spectrometry of the Stereoisomers of Heterocyclic Compounds. Part 2b. Perhydroxanthenes.

Nickolay S. Kulikov*, Marina S. Bobyleva

J. Chem. Soc., Perkin Trans. 2, p.955-958 (1998)

ABSTRACT: The quantitative relationships between the retention of the stereoisomers of perhydroxanthene (PHX) on the column packed with graphitized thermal carbon black (GTCB) and their hypothetical molecular structures optimized by molecular mechanics were established. From the GC-MS data obtained the structure of four novel stereoisomers have been elucidated. Along with the theoretically expected trans-anti-trans-, trans-cyn-cis- and cis-anti-cis-isomers, the unusual stable stereoisomeric form of PHX has been found and elucidated as conformer B of the cis-syn-cis-isomer. The evidence for this assignment based on the obtained GC- and MS-data is discussed.

Laboratory of Adsorption and Chromatography