1-(Trimethylsilyl)-2-propanone Chemische Eigenschaften,Einsatz,Produktion Methoden
Physikalische Eigenschaften
Clear liquid; bp 74 °C/96 mmHg; d 0.8274 g cm3
(26 °C), n26/D 1.4188.
Verwenden
Trimethylsilylacetone reacts with Grignard or organolithium reagents to provide, after
elimination, 2-substituted 2-propenes; in combination with
fluoride ion, gives chemistry of the corresponding enolate ion; can direct electrophilic substitution to either side of the carbonyl group, participating in (but not limited to) reactions: Preparation of 2-substituted α-Alkenes, Reaction with Electrophiles, Reaction with Fluoride Ion, Reaction with Strong Bases, etc.
synthetische
The best procedure for the preparation
of trimethylsilylacetone is the reaction of trimethylsilylmethylmagnesium
chloride or bromide with acetic anhydride.5
Other useful preparative methods for α-trimethylsilyl ketones
involve the reaction of trimethylsilylmethylmagnesium chloride
with acid chlorides,6 or with aldehydes followed by oxidation
of the resulting β-hydroxysilane to the ketone.2e When the
trialkylsilyl group is very large, particularly the triisopropylsilyl
group, a rearrangement from the silyl enol ether to the α-silyl
ketone is possible.
Vorsichtsma?nahmen
α-trimethylsilyl ketones thermally rearrange to the more stable silyl enol ethers at temperatures above approximately 100 °C and normally within 1 h at 140 °C or above; they hydrolyze to the parent ketone upon treatment with acid or base and are difficult to purify by chromatography due to desilylation; use in a fume hood.
1-(Trimethylsilyl)-2-propanone Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
