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Fluoroselenenylation of Acetylenes with Xenon Difluoride–Diorganyl Diselenides; Synthesis and Structure Elucidation of Functionalized Vicinal ( E )‐Fluoro(organylseleno)olefins
Author(s) -
Poleschner Helmut,
Heydenreich Matthias,
Schilde Uwe
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960719
Subject(s) - chemistry , tetrafluoroborate , vicinal , alkylation , difluoride , reagent , xenon difluoride , organic chemistry , medicinal chemistry , polymer chemistry , catalysis , ionic liquid
We 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 XeF 2 –R 2 Se 2 and XeF 2 –PhSeSiR 3 reagents proceeds via trans additions.