After a review of the intrinsic Lewis acidic properties of simple organoantimony compounds, we will show that the Lewis acidic properties of such compounds can be enhanced by both cooperative and electronic effects. The occurrence of cooperative effects will be showcased in a series of bidentate distiboranes which form fluoride complexes with remarkably stable Sb-F-Sb chelate motifs. The use of electronic effects will be illustrated by a discussion of the synthesis and chemistry of the stibonium cation [Sb(C6F5)4]+. This cation is a potent Lewis acid which abstracts a fluoride anion from [SbF6]- and [BF(C6F5)3]- indicating that it is a stronger Lewis acid than SbF5 and B(C6F5)3. This cation is also a powerful hydride abstracting agent which converts main group hydrides such as Et3SiH into the corresponding cations.

Lewis acidic properties of organoantimony compounds: From bidentate distiboranes to perfluorinated stibonium cations

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.