Pentafluoroethylated Compounds of Silicon, Germanium and Tin. Issue 62 (16th August 2018)

• Record Type: Journal Article
• Authors: Wiesemann, Markus; Hoge, Berthold
• Is Part Of: Chemistry. Volume 24:Issue 62(2018)
• Page Start: 16457
• Page End: 16471
• Publication Date: 2018-08-16
• Subjects: electron-deficient compounds -- fluorine -- germanium -- pentafluoroethyl -- silicon -- tin; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201801292
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: In this contribution we present an account on pentafluoroethylated compounds of silicon, germanium and tin. The pronounced electron‐withdrawing effect of the pentafluoroethyl group leads to a markedly increased Lewis acidity at the central atom which results in the stabilization of hypervalent complexes, anionic element(II) species as well as remarkable reactivities of element‐element and element‐hydrogen bonds. By addition to unsaturated C−C bonds or by reaction with organic halides as well as transition‐metal complexes the molecules bearing a pentafluoroethyl‐element group are readily accessible. Moreover, the utilization of pentafluoroethyl groups facilitates the formation of donor‐stabilized germylenes and stannylenes. A series of such compounds serves as suitable pentafluoroethylation reagents. Conversely to the well‐studied trifluoromethyl derivatives these compounds frequently exhibit a higher thermostability, which allows a more convenient handling. Abstract : The introduction of electron‐withdrawing pentafluoroethyl groups into organosilicon, organogermanium and organotin compounds creates a pronounced electron‐deficiency at the central atom, which leads to a significantly different chemical behavior with respect to non‐fluorinated derivatives. These characteristics facilitate the formation of hypervalent complexes, stabilization of low‐valent species as well as main group and transition‐metal complexes.