66166-06-1Relevant academic research and scientific papers
Reactions of RSe-EMe3 (E = Si, Ge, Sn, Pb) with XeF2 - RSe-F equivalents in the fluoroselenenylation of acetylenes
Poleschner, Helmut,Heydenreich, Matthias,Schilde, Uwe
, p. 1307 - 1313 (2007/10/03)
Selenides of the type R1Se-EMe3 (E = Si, Ge, Sn, Pb) react with xenon difluoride by cleavage of the Se-E bond to yield the R1Se-F intermediate and the fluorides Me3E-F, whereas the Se-C bond in PhSe-tBu (E = C) is stable against XeF2. The presence of R1Se-F intermediates is confirmed by addition to acetylenes (4-octyne, 3-hexyne). Thus, the fluoroselenenylation of acetylenes gives fluoro(organylseleno)olefins in preparative yields. In the cases of E = Si, Ge, Sn, and Pb, aryl and n-alkyl groups are suitable as the substituent R1. The X-ray crystal structural analysis of (E)-3-(p- carboxyphenylseleno)-4-fluorohex-3-ene - the first example of an uncharged fluoroselenoolefin synthesized from p-EtO2C-C6H4-Se-SnMe3, XeF2, and 3- hexyne followed by an ester hydrolysis - shows that the addition of the selenenylfluoride intermediate to the acetylene proceeds via a trans- addition, as is known for the R2Se2-XeF2 reagents.
