Bis(trimethylsilyl)peroxide

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Bis(trimethylsilyl)peroxide
Tms2O2.png
Names
Preferred IUPAC name
Peroxybis(trimethylsilane)
Identifiers
3D model (JSmol)
  • InChI=1S/C6H18O2Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3
    Key: XPEMYYBBHOILIJ-UHFFFAOYSA-N
  • C[Si](C)(C)OO[Si](C)(C)C
Properties
C6H18O2Si2
Molar mass 178.378 g·mol−1
Appearance colorless oil
Density 0.829 g/cm3
Boiling point 35 °C (95 °F; 308 K) 35 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bis(trimethylsilyl)peroxide (sometimes abbreviated as BTSP)[1] is an organosilicon compound with the formula ((CH3)3SiO)2. It is a colorless liquid that is soluble in organic solvents so long as they lack acidic groups. The compound represents an aprotic analogue of hydrogen peroxide and as such it is used for certain sensitive organic oxidations.[2] Upon treatment with organolithium compounds, it affords the silyl ether.

Preparation[edit]

It is prepared by treating trimethylsilyl chloride with the Hydrogen peroxide-urea complex.[3]

References[edit]

  1. ^ Baj, Stefan; Chrobok, Anna; Słupska, Roksana (2009-02-01). "The Baeyer–Villiger oxidation of ketones with bis(trimethylsilyl) peroxide in the presence of ionic liquids as the solvent and catalyst". Green Chemistry. 11 (2): 279–282. doi:10.1039/B814534B. ISSN 1463-9270.
  2. ^ Ishikawa, Hayato; Elliott, Gregory I.; Velcicky, Juraj; Choi, Younggi; Boger, Dale L. (2006). "Total Synthesis of (−)- andent-(+)-Vindoline and Related Alkaloids". Journal of the American Chemical Society. 128 (32): 10596–10612. doi:10.1021/ja061256t. PMC 2531198. PMID 16895428.
  3. ^ Jih Ru Hwu, Buh-Luen Chen, Santhosh F. Neelamkavil, Yuzhong Chen (2002). "Bis(trimethylsilyl) Peroxide". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb219.pub3. ISBN 0471936235.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)