Trimethylsilyl cyanide

Structure

The molecule exhibits the structure of a nitrile-like compound, having the structural formula . The compound exists in a rapid equilibrium with a small amount of the isomeric isocyanide . By contrast, the nearly isostructural tert-butyl nitrile does not readily isomerize to tert-butyl isocyanide. The isocyanide isomer can be stabilized by complexation to metals.

Reactions

Trimethylsilyl cyanide hydrolyzes to give hydrogen cyanide and trimethylsilanol: :

In its principal application, it adds across carbon-oxygen double bonds, for example in an aldehyde, to form a new carbon-carbon bond: : + (CH3)3SiC≡N → N≡C–Si(CH3)3 The product is an O-silylated cyanohydrin.

One use of this reagent is to convert pyridine-N-oxides into 2-cyanopyridine. This transformation is best done in dichloromethane solution using dimethylcarbamoyl chloride as the activating electrophile. It is possible to use benzoyl chloride but the yields and regioselectivity of the addition of the cyano group are lower.

Acetone cyanohydrin can be used to reversibly generate the cyanide anion. (4)[[File:CNAddScope1.png|center]]

Safety

Trimethylsilyl cyanide behaves equivalently to hydrogen cyanide, a potent poison.

References

References

1. Livinghouse, T.. (1981). "Trimethylsilyl Cyanide: Cyanosilation of p-Benzoquinone".
2. (2011). "Encyclopedia of Reagents for Organic Synthesis".
3. (1968). "Trimethylsilyl isocyanide". [[Chem. Commun.]].
4. (2018). "Synthesis and Characterization of Cyano and Isocyano Complexes of Bis(dithiolato) Molybdenum Using Me₃SiCN: A Route to a Cyanide-Bridged Multimer to a Monomer". New Journal of Chemistry.
5. Nazarov, N. ; Zav'yalov, I. ''J. Gen. Chem. USSR (Engl. Transl.)'' '''1954''', ''24'', 475 [C.A., 49, 6139f (1955)].
6. The compound can be disposed of by using a mixture of alkali hydroxide and bleach.[https://www.gelest.com/wp-content/uploads/product_msds/SIT8585.1-msds.pdf MSDS of trimethylsilyl cyanide. (PDF)]. Gelest. [Jun 13, 2019]