Premium
Persistent Dialkylsilanone Generated by Dehydrobromination of Dialkylbromosilanol
Author(s) -
Ishida Shintaro,
Abe Takashi,
Hirakawa Fumiya,
Kosai Tomoyuki,
Sato Katsuhiro,
Kira Mitsuo,
Iwamoto Takeaki
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501478
Subject(s) - silylation , toluene , isomerization , trimethylsilyl , chemistry , tris , medicinal chemistry , silicon , oxide , nuclear magnetic resonance spectroscopy , organic chemistry , photochemistry , catalysis , biochemistry
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 29 Si NMR spectrum in [D 8 ]toluene, the signal due to the unsaturated silicon nuclei was observed at 128.7 ppm. Reactions of the dialkylsilanone with water and mesitonitrile oxide gave a silanediol and a [2+3] cycloadduct, respectively. The silanone remains intact in [D 8 ]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.