Fluoroselenenylation of Acetylenes with Xenon Difluoride–Diorganyl Diselenides; Synthesis and Structure Elucidation of Functionalized Vicinal ( E )‐Fluoro(organylseleno)olefins | Zendy

Poleschner Helmut | Zendy; Heydenreich Matthias | Zendy; Schilde Uwe | Zendy

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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.

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