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Chemical Compound Review

TMSCN     trimethylsilylmethanenitrile

Synonyms: TMS cyanide, PubChem16763, ACMC-1BC54, AG-H-06602, ANW-36883, ...
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High impact information on trimethylsilylmethanenitrile

  • [reaction: see text] An environmentally benign and highly efficient procedure for the nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction) has been developed under biomimetic conditions in water in the presence of beta-cyclodextrin to afford alpha-aminonitriles in quantitative yields [1].
  • [reaction: see text] 2,3,5-Trisubstituted pyrroles were prepared in a regioselective manner using the double nucleophilic addition of alpha,alpha-dialkoxy ketene silyl acetals and ketene sily thioacetals or trimethylsilyl cyanide to alpha,beta-unsaturated imines followed by acid-promoted cyclization and oxidation with DDQ [2].

Associations of trimethylsilylmethanenitrile with other chemical compounds

  • This new methodology involves, as a key step, the synthesis of 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepines by a one-pot cyano reduction and reductive cyclization of the appropriate amino nitrile, which were obtained via a modified Strecker reaction of N-protected alpha-amino aldehydes with 2-aminobenzophenone and trimethylsilyl cyanide [3].


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