Collect. Czech. Chem. Commun. 1979, 44, 3595-3603

The role of conformational mobility in the stereospecific loss of water under electron impact

František Turečeka, Vladimír Hanuša and Miloš Tichýb

a J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 121 38 Prague 2
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Mass spectra of nine of the sixteen possible diastereoisomeric 7-hydroxytricyclo[,6]dodecanes are reported. The spectra differ considerably in the extent of water elimination from molecular ions. The diastereoisomers which have conformationally flexible cis-anti-cis, cis-anti-trans and cis-syn-trans skeletons exhibit abundant (M-H2O)+. ions. Molecular ions of the rigid trans-anti-trans isomers lose water to a markedly smaller extent, the main fragmentation proceeding via a skeletal cleavage. Effects of conformational mobility are emphasized.