Acylsilane

Acylsilanes are a group of chemical compounds sharing a common functional group with the general structure R(CO)-SiR3. Acylsilanes are starting compounds in the Brook rearrangement with vinyl lithium compounds to silyl enol ethers.

The structure of a typical acylsilane.

Synthesis

Acylsilanes can be synthesized using the following procedures:

Starting with the 1,3-dithiane, substituting with the silyl group, then removing the dithioacetal group with mercury(II) chloride and hydrolysis.[1] This method also can make acylgermanes using the appropriate halogermane reagents.

Brook acylsilane synthesis scheme. Also can be used for synthesizing acylgermanes.

Another method was reported by Kuwajima et al[2] using 1,1-bis(trimethylsilyl)alkan-1-ols. t-Butyl hypochlorite converts the starting material to the acylsilane.

Kuwajima acylsilane synthesis, with the method to make the 1,1-bis(trimethylsilyl)alkan-1-ol.

References
  1. Brook, A. G. (Jan 1, 1967). "Synthesis of Silyl and Germyl Ketones". Journal of the American Chemical Society. 89 (2): 431–434. doi:10.1021/ja00978a047.
  2. Kuwajima, Isao; Abe, Toru; Minami, Naoki (1976-09-05). "AN EFFICIENT METHOD FOR THE PREPARATION OF ACYLSILANE AND α-HALOACYLSILANE". Chemistry Letters. 5 (9): 993–994. doi:10.1246/cl.1976.993. ISSN 0366-7022.

^ The reactivity of α- and β-iodo propenoylsilanes: an alternative access to polyunsaturated acylsilanes Alessandro Degl’Innocenti, Antonella Capperucci, Patrizia Scafato,Antonella Telesca Arkivoc 0-005A 2000 Article

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