2026/05/13 by Leif Kelling, Mike Jörges, Viktoria H. Gessner · 1 voice
Pharmacology, Toxicology and Pharmaceutics · Chemistry · Biochemistry, Genetics and Molecular Biology · #Bioactive Compounds and Antitumor Agents #Cyclization and Aryne Chemistry #Coenzyme Q10 studies and effects
paper · pdf · doi:10.1021/acs.organomet.6c00081
openalex publication_date 2026/05/13 · openalex created_date 2026/05/14 · openalex updated_date 2026/07/02
High Resolution Image Download MS PowerPoint Slide Despite the importance of quinones in organic synthesis and materials chemistry, their silicon analogues remain largely unexplored to date. Herein, we report the synthesis of two base-coordinated 1,4-disilaquinones through dimerization of ketenyl-substituted silylenes, which were in situ generated by reaction of two differently substituted metalated ketenes with the amidinato-stabilized chlorosilylene (PhC(NtBu) 2 SiCl). X-ray crystallography combined with density functional theory (DFT) calculations revealed a planar but unsymmetrical structure of the disilaquinone core, arising from its unusual bonding situation. The central heterocyclic motif is best described as a resonance hybrid of three principal forms: a silaquinone-type structure or as a dimer of two enolates and carbanionic ketones, respectively. Despite its nonaromatic character, the disilaquinone core exhibits remarkable thermal and chemical stability, showing no tendency toward ring-opening. Although unreactive toward nucleophiles, treatment with Lewis or Brønsted acids perturbs the π-electron density but preserves the integrity of the six-membered ring scaffold.