Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1315029 | Journal of Fluorine Chemistry | 2010 | 4 Pages |
Chlorotrifluoroethene is converted in situ to [F2CCFSiMe3]. The crude [F2CCFSiMe3] solution is reduced with lithium aluminum hydride to (HFCCFSiMe3), which (without isolation) is converted to (Z)-HFCCFSnBu3. Subsequent metallation and trapping of the vinyllithium reagent with Bu3SnCl gives (E)-Bu3SnCFCFSnBu3 in 73% overall yield. Only two isolation steps are required and the use of Me3SiCl and F2CCFCl provides a cheap, economical route to this useful synthon.
Graphical abstractChlorotrifluoroethene is converted in situ to [F2CCFSiMe3]. The crude [F2CCFSiMe3] solution is reduced with lithium aluminum hydride to (HFCCFSiMe3), which (without isolation) is converted to (Z)-HFCCFSnBu3. Subsequent metallation and trapping of the vinyllithium reagent with Bu3SnCl gives (E)-Bu3SnCFCFSnBu3 in 73% overall yield. Only two isolation steps are required and the use of Me3SiCl and F2CCFCl provides a cheap, economical route to this useful synthon.Figure optionsDownload full-size imageDownload as PowerPoint slide