Persistent Dialkylsilanone Generated by Dehydrobromination of Dialkylbromosilanol

Shintaro Ishida, Takashi Abe, Fumiya Hirakawa, Tomoyuki Kosai, Katsuhiro Sato, Mitsuo Kira, Takeaki Iwamoto

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A persistent dialkylsilanone was synthesized by the dehydrobromination of a dialkylbromosilanol with tris(trimethylsilyl)silyl potassium in solution at -80°C: It was characterized by NMR and IR spectroscopy, and was tested in several reactions. In 29Si NMR spectrum in [D8]toluene, the signal due to the unsaturated silicon nuclei was observed at 128.7ppm. Reactions of the dialkylsilanone with water and mesitonitrile oxide gave a silanediol and a [2+3] cycloadduct, respectively. The silanone remains intact in [D8]toluene below -80°C for at least two days, while it undergoes unprecedented isomerization to give a siloxysilene by means of 1,3-silyl migration at higher temperatures. Persistent diorganosilanone in solution! A persistent diorganosilanone was synthesized by a new synthetic method, dehydrobromination of the corresponding diorganobromosilanol with tris(trimethylsilyl)silyl potassium in solution at -80°C (see scheme). The silanone was characterized by NMR and IR spectroscopy, and by chemical trapping. In 29Si NMR spectrum in [D8]toluene, the signal due to the unsaturated silicon nuclei was observed at 128.7ppm.

Original languageEnglish
Pages (from-to)15100-15103
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number43
DOIs
Publication statusPublished - 2015 Oct 1

Keywords

  • cycloaddition
  • ketones
  • multiple bonds
  • silanone

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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