Abstract
AbstractWe carried out the fluoroselenenylation of hex‐3‐yne with xenon difluoride and functionalized diselenides (dimethyl acetal‐ and carboxylic acid ester‐substituted) to the corresponding substituted vicinal (E)‐fluoro(organylseleno)olefins. Consecutive reactions afforded crystalline 2,4‐dinitrophenylhydrazone and carboxylic acid derivatives. Nonfunctionalized vicinal (E)‐fluoro(organylseleno)olefins were alkylated with trimethyloxonium tetrafluoroborate, triethyloxonium tetrafluoroborate, and methyl trifluoromethanesulfonate to the corresponding fluoroalkenyldiorganylselenonium salts which were characterized either as tetrafluoroborate or as tetraphenylborate salts. X‐ray analysis of [(E)‐4‐fluorooct‐4‐en‐5‐yl]dimethylselenonium picrate (11) proved unambiguously that the fluoroselenenylation of acetylenes with XeF2–R2Se2 and XeF2–PhSeSiR3 reagents proceeds via trans additions.
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