Ketenimines

Ketenimines are a group of organic compounds with the general structure R2C=C=NR'. 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:

Ph3P=CR2 + R'N=C=O → R2C=C=NR' + Ph3PO (Ph = phenyl)

Similarly, aza-Wittig reagents react with ketenes to give ketenimines:

Ph3P=NR' + R2C=C=O → R2C=C=NR' + Ph3PO

This method was employed in the preparation of the first example of a ketenimine.

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