Synthesis and Reactions of Ketenimines

Abstract Ketenimines R1R2CCNR3 were first reported in 1919, but the development of the chemistry of these compounds is of relatively recent origin. These heterocumulenes are becoming of increasing interest as a dehydrating agent for peptide syntheses, as a coreagent in dimethyl sulfoxide oxidations, and as a substrate in the synthesis of heterocycles by condensation with polar multiple bonds and dipolar systems. The cycloadditions are of special interest from the viewpoint of orbital symmetry considerations. Some unusual organometallic complexes of ketenimines have also been synthesized. Recently some triaryl ketenimines have been found to have insecticidal and miticidal activity. Polymeric ketenimines have been implicated as molecular precursors of life.