Acylsilane on:
[Wikipedia]
[Google]
[Amazon]
Acylsilanes are a group of
Another method was reported by Kuwajima ''et al.'' using 1,1-bis(trimethylsilyl)alkan-1-ols. ''t''-Butyl hypochlorite converts the starting material to the acylsilane.
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
s sharing a common functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
with the general structure R(CO)-SiR3. Acylsilanes are starting compounds in the Brook rearrangement In organic chemistry the Brook rearrangement refers to any ,''n''carbon to oxygen silyl migration. The Rearrangement reaction, rearrangement was first observed in the late 1950s by Canadian chemist Adrian Gibbs Brook (1924–2013), after which t ...
with vinyl
Vinyl may refer to:
Chemistry
* Polyvinyl chloride (PVC), a particular vinyl polymer
* Vinyl cation, a type of carbocation
* Vinyl group, a broad class of organic molecules in chemistry
* Vinyl polymer, a group of polymers derived from vinyl m ...
lithium
Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid el ...
compounds to silyl enol ether
Silyl enol ethers in organic chemistry are a class of organic compounds that share a common functional group composed of an enolate bonded through its oxygen end to an organosilicon group. They are important intermediates in organic synthesis.
Syn ...
s.
Synthesis
Acylsilanes can be synthesized using the following procedures: Starting with the1,3-dithiane
A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-- units) are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane.
1 ...
, substituting with the silyl group, then removing the dithioacetal group with mercury(II) chloride
Mercury(II) chloride (or mercury bichloride, mercury dichloride), historically also known as sulema or corrosive sublimate, is the inorganic chemical compound of mercury and chlorine with the formula HgCl2. It is white crystalline solid and is ...
and hydrolysis. This method also can make acylgermanes using the appropriate halogermane reagents.
Another method was reported by Kuwajima ''et al.'' using 1,1-bis(trimethylsilyl)alkan-1-ols. ''t''-Butyl hypochlorite converts the starting material to the acylsilane.
References
{{Reflist Functional groups Organosilicon compounds