Syntheses and Mass Spectral Studies of (E)-1-Alkanesulfonylpropenes and (E)-1-Alkanesulfinylpropenes

(E)-1-Alkanesulfonylpropenes and (E)-1-Alkanesulfinylpropenes have been synthesized in good to excellent yields. Studies correlating molecular structure and fragmentation patterns upon electron impact have been carried out. Double hydrogen rearrangements with the elimination of alkenyl radicals are the most facile fragmentations for (E)-1-alkanesulfonylpropenes. Single hydrogen rearrangement with alkene elemination is however the most important fragmentation for (E)-1-alkanesulfinylpropenes. In this case the hydrogen atom only migrates to the sulfinyl oxygen. These differences in fragmentation patterns between the (E)-styryl-alkyl-sulfones/sulfoxides and the (E)-propenyl-alkyl-sulfones/sulfoxides are attributed to the fact that different ionization sites are involved.