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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom