13C, 19F and 77Se NMR study of vicinal (E)-fluoro(organylseleno)olefins and [(E)- fluoroalkenyl]diorganylselenonium salts
- 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.
Author details: | Helmut Poleschner, Matthias HeydenreichORCiD, Uwe SchildeORCiDGND |
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Publication type: | Article |
Language: | English |
Year of first publication: | 2000 |
Publication year: | 2000 |
Release date: | 2017/03/24 |
Source: | European Journal of Inorganic Chemistry. - (2000), S. 1307 - 1313 |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
Institution name at the time of the publication: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Organische Chemie und Strukturanalytik |