Surf Wiki
Save to docs
general/alkyne-derivatives

From Surf Wiki (app.surf) — the open knowledge base

Bis(trimethylsilyl)acetylene

Bis(trimethylsilyl)acetylene (BTMSA) is an organosilicon compound with the formula Me3SiC≡CSiMe3 (Me = methyl). It is a crystalline solid that melts slightly above room temperature and is soluble in organic solvents. This compound is used as a surrogate for acetylene.

BTMSA is prepared by treating acetylene with butyllithium followed by addition of trimethylsilyl chloride (Me = CH3, Bu = C4H9): :HC≡CH + 2 BuLi → LiC≡CLi + 2 BuH :LiC≡CLi + 2 Me3SiCl → Me3SiC≡CSiMe3 + 2 LiCl

Reactions

BTMSA is used as a nucleophile in Friedel-Crafts type acylations and alkylations and a precursor to lithium trimethylsilylacetylide. The TMS groups can be removed with tetra-n-butylammonium fluoride (TBAF) and replaced with protons. BTMSA is also a useful reagent in cycloaddition reactions. Illustrating its versatility, BTMSA was used in a concise total synthesis of (±)-estrone. A key step in this synthesis was the formation of the steroidal skeleton, catalyzed by CpCo(CO)2.

BTMSA also serves as a ligand in organometallic chemistry. For example, it forms stable adducts with metallocenes. : Cp2TiCl2 + Mg + Me3SiC≡CSiMe3 → Cp2Ti(η²-Me3SiC₂SiMe3) + MgCl2

References

References

  1. (1972). "Friedel–Crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones". Journal of Organometallic Chemistry.
  2. (2008). "Encyclopedia of Reagents for Organic Synthesis".
  3. (2003). "The Titanocene Complex of Bis(trimethylsilyl)acetylene: Synthesis, Structure, and Chemistry". Organometallics.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alkyne-derivatives trimethylsilyl-compounds
Want to explore this topic further?

Ask Mako anything about Bis(trimethylsilyl)acetylene — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report