Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 2b.¹ Perhydroxanthenes

Abstract

The quantitative relationships between the retention of the stereoisomers of perhydroxanthene (PHX) on a column packed with graphitized thermal carbon black (GTCB) and their hypothetical molecular structures optimized by molecular mechanics have been 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-syn-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.

References

1. Part 2a: M. S. BobylevaN. S. KulidovJ. Chem. Soc., Perkin Trans. 2, preceding paper.
2. Part 1: V. G. Adeeva, M. S. Bobyleva, M. S. Kulikov, V. G. Kharchenko and L. M. Yudovich, J. Chem. Soc., Perkin Trans. 2, 1992, 965.
3. A. V. Kiselev and D. P. Poshkus, Faraday Symp. Chem. Soc., 1980, 15, 13.
4. A. V. Kiselev, Physical Chemistry, Modern Problems, Khimiya, Moscow (in Russian), 1982.
5. N. S. Kulikov, Adsorpt. Sci. Technol., 1997, 15, 115.
6. A. V. Kiselev and N. S. Kulikov, Dokl. Acad. Nauk SSSR, 1982, 266, 153.
7. N. N. Avgul, A. V. Kiselev and D. P. Poshkus, Adsorption of Gases and Vapors on Uniform Surfaces, Khimia, Moscow (in Russian), 1976.
8. P. B. Dallakyan, R. S. Petrova and V. L. Khudyakov, Zh. Fiz. Khim., 1988, 62, 2272.
9. A. V. Kiselev, D. P. Poshkus and A. Ya. Afreimovich, Zh. Fiz. Khim., 1968, 42, 2546.
10. A. V. Kiselev, N. S. Kulikov and G. Curthoys, Chromatographia, 1984, 18, 297.