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Ketenimines

Class of chemical compounds

Ketenimines
Summary

Class of chemical compounds

General structure of a ketenimine

Ketenimines are a group of organic compounds with the general structure . A ketenimine is a cumulated alkene and imine and is related to an allene and a ketene. When the substituents on the terminal carbon differ, the ketenimines are intrinsically chiral owing to the non-linearity of the C=N-R group.

Ketenimines can be prepared by reactions of isocyanates with Wittig reagents: : (Ph = phenyl) Similarly, aza-Wittig reagents react with ketenes to give ketenimines: : This method was employed in the preparation of the first example of a ketenimine.

Astronomical detection

The parent ketenimine (CH2CNH) has a distinctive rovibrational spectrum. The ν8 and ν12 bands in the high-resolution FTIR spectrum are pair of Coriolis-coupled bands. They provide a rare example where intensity sharing between bands yields sufficient intensity for an otherwise invisible band (ν12).

References

References

  1. (2012). "The Thriving Chemistry of Ketenimines". Chemical Society Reviews.
  2. (1919). "Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine". Helvetica Chimica Acta.
  3. (2011). "High-resolution FTIR spectroscopy of the ν8 and Coriolis perturbation allowed ν12 bands of ketenimine". Physical Chemistry Chemical Physics.
  4. (2006). "Detection of Ketenimine (CH2CNH) in Sagittarius B2(N) Hot Cores". The Astrophysical Journal.
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functional-groups imino-compounds heterocumulenes
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