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Synthesis 1994; 1994(10): 1043-1049
DOI: 10.1055/s-1994-25635
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Fluoroselenenylation of Acetylenes with Xenon Difluoride-Diorganyl Diselenides and Xenon Difluoride-Phenylseleno(trialkyl)silanes

Helmut Poleschner* , Matthias Heydenreich, Karla Spindler, Günter Haufe
  • *Universität Potsdam, Projektgruppe Naturstoffe, Stahnsdorfer Damm 81, D-14532 Kleinmachnow, Germany
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Publication Date:
27 September 2002 (online)

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A new, efficient method of fluoroselenenylation of terminal, and open-chain symmetric and unsymmetric disubstituted acetylenes and cycloalkynes, gives vicinal (E)-fluoroalkenyl selenides in moderate to high yields by addition of selenenyl fluoride equivalents. These are formed in situ from xenon difluoride and diaryl, dibenzyl or primary and secondary dialkyl diselenides. Alternatively, the benzeneselenenyl fluoride equivalent is formed by treatment of more reactive phenylselenotrialkylsilanes with xenon difluoride. The regiochemistry of the addition is strongly dependent on the steric effects of substituents bonded to the acetylene.