Abstract
Abstract Mass spectra of six cyclic sulfoxides were determined in order to study the effects of ring size on the rate of OH-elimination from molecular ions. The ratios of the rates for the OH loss, [M+–OH]/[M+], are: trimethylene sulfoxide: 0.23/tetramethylene sulfoxide: 0.06/pentamethylene sulfoxide: 0.24 /hexamethylene sulfoxide: 1.21/9-thiamonoxybicyclo[3.3.1]nonane: 3.14/7-thiamonoxybicyclo[2.2.1]heptane: 0.02. These findings were explained in terms of the difference in the closest approaching distance between the sulfinyl oxygen and the β- or γ-hydrogen atoms. Geometry of the ionized molecular ions appears to be an important factor in determining these ratios. The loss of HSO was also disucssed.
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