72189-54-9

Usage

Chemical class

Organosilicon compounds

Unique feature

Contains an unusual silicon-carbon double bond

Application

Used in organic synthesis as a reactive intermediate and as a building block for creating more complex molecules

Stability

Stable under normal conditions and can be stored for extended periods

Structure

Unique structure that contributes to its reactivity

Reactivity

Valuable tool for the development of new materials and pharmaceuticals

Research contribution

Has contributed to a deeper understanding of the properties and reactivity of organosilicon compounds

InChI:InChI=1/C20H42OSi4/c1-23(2,3)21-19(22(24(4,5)6)25(7,8)9)20-13-16-10-17(14-20)12-18(11-16)15-20/h16-18H,10-15H2,1-9H3

Upstream product

• 4110-02-5 tris(trimethylsilyl)silyllithium 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 72189-53-8 1-adamantanecarbonyltris(trimethylsilyl)silane 

Downstream Products

• 1118145-92-8 C₃₁H₅₂OSi₄ 
• 1118145-94-0 C₅₃H₉₈O₃Si₈ 

Relevant academic research and scientific papers

Preliminary communication. Silacyclopropanes from the reaction of silenes with Wittig reagents

The stable silene (Me3Si)2Si=C(OSiMe3)Ad (Ad = adamantyl) was found to react with the phosphorous ylid Ph3P+CH2- or its sulfur analog to form the related silacyclopropane, as shown by NMR spectroscopy and by derivatization with methanol or acetophenone.

Stable Solid Silaethylenes

A solid silaethylene, 1,1-bis(trimethylsilyl)-2-(trimethylsiloxy)-1-(1-adamantyl)-1-silaethene (2c), has been isolated from the photolysis of the isomeric acylsilane.The silaethylene was characterized by IR, Raman, UV, 1H NMR, 13C NMR, 29Si NMR, and mass spectroscopy and by its ionization potential.The crystal structure shows a slightly twisted molecule with a silicn-carbon double-bond length of 1.764 Angstroem.The molecule smokes vigorously in air, yielding a cyclic trisiloxane and the silyl ester of adamantane-1-carboxylic acid.Other reactions and comparisons with other silaethylenes in solution are described.In addition, 1,1-bis(trimethylsilyl)-2-(trimethylsiloxy)-2-(1,1-diethylpropyl)-1-silaethene (2b) has been obtained as a solid.

A Solid Silaethene: Isolation and Characterization

The first reported solid silaethene, m.p. 95 deg C, stable at room temperature under argon, but highly reactive in air has been isolated and characterized by i.r., n.m.r. and mass spectrometry.