Sila-Peterson Reaction of Cyclic Silanides

Andreas W. Kyri, Lukas Schuh, Andreas Knoechl, Michael Schalli, Ana Torvisco, Roland C. Fischer, Michael Haas, Harald Stueger*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

Sila-Peterson type reactions of the 1,4,4-tris(trimethylsilyl)-1-metallooctamethylcyclohexasilanes (Me3Si)2Si6Me8(SiMe3)M (2a, M = Li; 2b, M = K) with various ketones were investigated. The obtained products strongly depend on the nature of the ketone component. With 2-adamantanone 2a,b afforded the moderately stable silene 3. 3 is the first example of an Apeloig-Ishikawa-Oehme-type silene with the tricoordinate silicon atom incorporated into a cyclopolysilane framework and could be characterized by NMR and UV spectroscopy as well as by trapping reactions with water, methanol, and MeLi. The reaction of 2b with aromatic ketones also follows a sila-Peterson type mechanism with formation of carbanionic species. With 1,2-diphenylcyclopropenone 2b reacted by conjugate 1,4-addition to give a spirocyclic carbanion. In most cases the underlying reaction mechanism could be elucidated by the isolation and characterization of unstable intermediates and final products after proper derivatization.

Original languageEnglish
Pages (from-to)1832-1841
Number of pages10
JournalOrganometallics
Volume39
Issue number10
DOIs
Publication statusPublished - 26 May 2020

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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