Collect. Czech. Chem. Commun. 1982, 47, 2946-2960

Inductive effect in EI-mass spectra of some 5,6-dihalogenides and 5,6-halohydrins of 5α-cholestan-3β-ol and 3β-acetoxy-5α-cholestane

Antonín Trka and Alexander Kasal

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Partial EI-mass spectra of 3β-hydroxy- and 3β-acetoxy-5α-cholestanes substituted in positions 5α-, 6β- or 5α,6β- with a hydroxyl group or halogen atoms (fluorine, chlorine, bromine) are presented. The molecular ions of 5α,6β-disubstituted derivatives of 3β-hydroxy-5α-cholestane (or of its 3-acetate) are considerably more stable than the corresponding monosubstituted derivatives if at least one of the pair of the vicinal substituents is chlorine or fluorine. This increase in stability, most striking in 5α- and 6β-fluoro compounds, is explained by the inductive effect.