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Neutral Homoaromatic Diboradisilacyclobutene: Synthesis, Structure, and Reactivity

Yu Zhang, Linlin Wu, Hao Wang

2022Journal of the American Chemical Society20 citationsDOI

Abstract

A formally neutral homoaromatic diboradisilacyclobutene was prepared and structurally characterized via the reduction of borylaminobromosilane with potassium graphite, which represents the first neutral boron and silicon mixed analogue of the homocyclopropenylium ion. Single-crystal X-ray analyses revealed a folded four-membered B2Si2 ring (26.2°) and a remarkably short transannular B–Si distance of 2.306(3) Å. DFT calculations showed that two π-electrons delocalize over the BSi2 moiety. Both structural feature and DFT calculations show the significant 2π-homoaromatic nature of the diboradisilacyclobutene. Furthermore, diboradisilacyclobutene reacted readily with CuCl or HCl to afford the diboradisilacyclobutanes.

Topics & Concepts

ChemistryMoietyBoronReactivity (psychology)Ring (chemistry)IonSiliconCrystallographyGraphitePotassiumCrystal structureSingle crystalElectronStereochemistryComputational chemistryMedicinal chemistryOrganic chemistryAlternative medicinePhysicsMedicineQuantum mechanicsPathologyOrganoboron and organosilicon chemistrySynthesis and characterization of novel inorganic/organometallic compoundsOrganometallic Complex Synthesis and Catalysis
Neutral Homoaromatic Diboradisilacyclobutene: Synthesis, Structure, and Reactivity | Litcius