title: Bridging the Gap between Bisylides and Methandiides: Isolation, Reactivity, and Electronic Structure of an Yldiide.
abstract: Bisylides and methandiides are two unique families of carbon bases that have found a variety of applications in recent years. Metalated ylides (yldiides) are the link between these types of compounds. Yet, only little is known about their properties, reactivities, and particularly their electronic structure. Here, we report the preparation of the metalated ylide [Ph3P-C-SO2Tol](-) (1) with different alkali metal counterions. The compounds have been studied by X-ray diffraction analysis and NMR spectroscopy and the first structures of a sodium and potassium yldiide are presented. The electronic structure of 1 was explored by DFT calculations confirming its relation with other divalent carbon species. Reactivity studies demonstrate the strong nucleophilicity of the yldiide and its capability to act both as a σ- and π-donor.
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.chemie.uni-wuerzburg.de/forschungsgruppen/dr_v_gessner/
authors.forename: Thorsten
authors.initials: T
authors.lastname: Scherpf
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.chemie.uni-wuerzburg.de/forschungsgruppen/dr_v_gessner/
authors.forename: Regina
authors.initials: R
authors.lastname: Wirth
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.chemie.uni-wuerzburg.de/forschungsgruppen/dr_v_gessner/
authors.forename: Sebastian
authors.initials: S
authors.lastname: Molitor
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.chemie.uni-wuerzburg.de/forschungsgruppen/dr_v_gessner/
authors.forename: Kai-Stephan
authors.initials: KS
authors.lastname: Feichtner
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany) http://www-anorganik.chemie.uni-wuerzburg.de/forschungsgruppen/dr_v_gessner/. vgessner@uni-wuerzburg.de.
authors.forename: Viktoria H
authors.initials: VH
authors.lastname: Gessner
mesh_terms: D018360:Crystallography, X-Ray; D004583:Electrons; D008672:Metals, Alkali / Q000737:chemistry*; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D008672:Metals, Alkali; D009942:Organometallic Compounds
keywords: alkali metals; carbanions; lithium; structure elucidation; ylides