Bis(trimethylsilyl) peroxide

Bis(trimethylsilyl) peroxide
Identifiers
CAS Number	5796-98-5;
3D model (JSmol)	Interactive image;
PubChem CID	10058088;
CompTox Dashboard (EPA)	DTXSID60434842 ;
	InChI InChI=1S/C6H18O2Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3 Key: XPEMYYBBHOILIJ-UHFFFAOYSA-N;
	SMILES C[Si](C)(C)OO[Si](C)(C)C;
Properties
Chemical formula	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).
	Infobox references

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 anhydrous adducts of hydrogen peroxide, e.g. Hydrogen peroxide-urea complex.[3]

References

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.
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.
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.CS1 maint: uses authors parameter (link)

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[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.CS1 maint: uses authors parameter (link)