Nitrilium

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The general structures of nitrilium ions

A nitrilium ion is a

alkylated, [RCNR′]+.[1]

Synthesis

Nitriles are only weakly basic[2] and are poor nucleophiles, but they will attack very reactive electrophiles such as carbocations.[3]

Nitrilium salts can be prepared by reacting nitriles with trialkyloxonium salts. The nitrilium ions thus formed can then be reduced to secondary amines with sodium borohydride in diglyme. This is a convenient route to secondary amines of the form RCH2—NH—R′.[4]

As intermediates

Nitrilium ions are believed to be intermediates in the hydrolysis of nitriles,

isoquinolines,[6] the Schmidt reaction with ketones,[7] and the Ugi, Ritter, Pinner and Passerini
reactions.

References

  1. IUPAC Gold Book: nitrilium ions
  2. ISBN 978-0-19-850346-0
    .
  3. ISBN 978-0-19-850346-0
    .
  4. ISBN 978-0-471-72091-1
    .
  5. ISBN 978-0-19-850346-0
    .
  6. ISBN 978-0-471-72091-1
    .
  7. ISBN 978-0-471-72091-1
    .
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