Bis(trimethylsilyl)peroxide explained

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

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

References

  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. en. 11. 2. 279–282. 10.1039/B814534B. 1463-9270.
  2. 10.1021/ja061256t. Total Synthesis of (−)- andent-(+)-Vindoline and Related Alkaloids. 2006. Ishikawa. Hayato. Elliott. Gregory I.. Velcicky. Juraj. Choi. Younggi. Boger. Dale L.. Journal of the American Chemical Society. 128. 32. 10596–10612. 16895428. 2531198.
  3. Encyclopedia: Bis(trimethylsilyl) Peroxide . Jih Ru Hwu . Buh-Luen Chen . Santhosh F. Neelamkavil . Yuzhong Chen. Encyclopedia of Reagents for Organic Synthesis. 2002. 10.1002/047084289X.rb219.pub3. 0-471-93623-5. e-EROS Encyclopedia of Reagents for Organic Synthesis.

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