H. Poleschner et al., FLUOROSELENENYLATION OF ACETYLENES WITH XENON DIFLUORIDE-DIORGANYL DISELENIDES AND XENON DIFLUORIDE-PHENYLSELENO (TRIALKYL)SILANES, Synthesis, (10), 1994, pp. 1043-1049
A new, efficient method of fluoroselenenylation of terminal, and open-
chain symmetric and unsymmetric disubstituted acetylenes and cycloalky
nes, gives vicinal (E)-fluoroalkenyl selenides in moderate to high yie
lds by addition of selenenyl fluoride equivalents. These are formed in
situ from xenon difluoride and diaryl, dibenzyl or primary and second
ary dialkyl diselenides. Alternatively, the benzeneselenenyl fluoride
equivalent is formed by treatment of more reactive phenylselenotrialky
lsilanes with xenon difluoride. The regiochemistry of the addition is
strongly dependent on the steric effects of substituents bonded to the
acetylene.