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Methyl isocyanide

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Title: Methyl isocyanide  
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Subject: Ammonia, Solvents, Methanol, Diazenylium, Silicon monosulfide
Collection: Hazardous Air Pollutants, Isocyanides, Solvents
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Methyl isocyanide

Methyl isocyanide or Isocyanomethane is an isocyanide family. This colorless liquid is isomeric to methyl cyanide (acetonitrile), but its reactivity is very different. Methyl isocyanide is mainly used for making 5-membered heterocyclic rings. The C-N distance in methyl isocyanides is very short, 1.158 Å as is characteristic of isocyanides.[1]

Preparation and uses

Methyl isocyanide was first prepared Gautier by reaction of silver cyanide with methyl iodide.[2][3] The common method for preparing methyl isocyanides is the dehydration of N-methylformamide.[4]

Methyl isocyanide is useful for the preparation of diverse heterocycles. It is also a ligand in organometallic chemistry.[5]

References

  1. ^ Myer Kessler, Harold Ring, Ralph Trambarulo, Walter Gordy "Microwave Spectra and Molecular Structures of Methyl Cyanide and Methyl Isocyanide" Phys. Rev. 1950, vol. 79, 54–56.
  2. ^ Gautier, A. (1868). "Ueber eine neue Reihe von Verbindungen, welche mit den Cyanwasserstoffsäure-Aethern isomer sind".  
  3. ^ Gautier, A. (1869). "Des Nitriles des Acides Gras: Dieuxiéme Partie - Des Carbylamines".  
  4. ^ Schuster, R. E.; Scott, J. E. (1966), "Methyl isocyanide",  
  5. ^ Eckert, H.; Nestl, A.; Ugi, I. (2001). "Methyl isocyanide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons.  

External links

  • N"3H2"WebBook page for C. 
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