Triethylsilane is used for the hydrosilation of olefins to prepare alkyl silanes. It acts as a reducing agent in the reduction of 2-chromanols, since it has an active hydride. It acts as a catalyst for redox initiated cationic polymerization, regioselective reductive coupling of enones and allenes, and Beckmann rearrangement of cyclododecanone oxime. It is associated with trifluoroacetic acid and involved in the selective reduction of alkenes.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Triethylsilane is used for the hydrosilation of olefins to prepare alkyl silanes. It acts as a reducing agent in the reduction of 2-chromanols, since it has an active hydride. It acts as a catalyst for redox initiated cationic polymerization, regioselective reductive coupling of enones and allenes, and Beckmann rearrangement of cyclododecanone oxime. It is associated with trifluoroacetic acid and involved in the selective reduction of alkenes.
Solubility
Miscible with water.
Notes
Incompatible with strong acids, water and bases.
RUO – Research Use Only
General References:
- In combination with TFA, ionic hydrogenation of alkenes occurs. This can be a useful alternative to catalytic hydrogenation, since selective reduction, e.g. of the more branched double bond of a diene can be achieved. For a review of ionic hydrogenation, see: Synthesis, 633 (1974):
- For trans-hydrosilylation of alkynes, catalyzed by AlCl3, see: J. Org. Chem., 61, 7354 (1996); 64, 2494 (1999).
- ɑß-Enones are reduced selectively to saturated ketones In the presence of TFA: Synthesis, 420 (1973); or Wilkinson's catalyst (Chlorotris(triphenyl phosphine) rhodium(I) , 10468): Tetrahedron Lett., 5035 (1972); Organometallics, 1, 1390 (1982).