Mass Spectra of Bicyclo[2.2.1 ]-2-heptanols

The fragmentation of bicyclo[2.2.1]-2-heptanol, endo- (I) and exo- (Ia), 1-methylbicyclo[2.2.1]-2-heptanol, endo- (II) and exo( IIa) and 2-methylbicyclo[2.2.1]-2-heptanol, endo- (III) has been studied by employing the deuterium labelling technique. The results obtained indicate · that the existence of nonclassical carbonium ion is of no significant importance during the fragmentation of the molecular ion of these alcohols and that the dehydration of the molecular ion is stereospecific regarding the position of eliminated hydrogen