Trimethylsilyl cyanide, 97%, Thermo Scientific Chemicals

General References:

1. Reagent for the formation of O-TMS cyanohydrins from carbonyl compounds.
2. The ZnI₂-catalyzed procedure allows cyanohydrins of unreactive ketones to be prepared in good yield, avoiding the unfavourable equilibria often encountered with the classical alkali cyanide method. For details and list of examples, see: Org. Synth. Coll., 7, 20 (1990). Other catalysts including Et₃N or Bu₃P are also effective: Chem. Lett., 537, 541 (1991). For catalysis by Methyl triphenyl phosphonium iodide, A15644 , see: Tetrahedron Lett., 44, 6157 (2003). In the absence of a catalyst, aldehydes have been found to give good yields of the TMS cyanohydrin, but reaction with ketones is very slow: J. Chem. Soc., Perkin 1, 2383 (1995). For use of Tetracyanoethyl ene, A13945 , as a ã-acid catalyst for both aldehydes and ketones, see: J. Chem. Soc., Perkin 1, 2155 (1995). Under the same conditions, dimethyl acetals give O-methyl cyanohydrins.
3. For examples of transformations of ketone TMS cyanohydrins, see: Chem. Pharm. Bull., 43, 1294 (1995).
4. For use in asymmetric Strecker synthesis of chiral amino acids, see: Tetrahedron Lett., 29, 4397 (1988).
5. Tertiary alkyl halides normally undergo elimination when treated with alkali cyanides, but can be converted to the corresponding nitriles by reaction with TMSCN in the presence of SnCl₄: Angew. Chem. Int. Ed., 20, 117 (1981).
6. Reacts with epoxides in the presence of ZnI₂ to give trans-ɑ-siloxy isocyanides, which can be readily hydrolyzed to the hydroxy isocyanides: J. Am. Chem. Soc., 104, 5849 (1982); Org. Synth. Coll., 7, 294 (1990). In the presence of Ag salts (AgClO₄, AgBF₄ or AgOTf), alkenes can be converted to isocyanides in Markovnikov fashion: Synlett, 288 (1999).
7. For a brief survey of uses of this reagent in synthesis, see: Synlett, 1625 (2007).