Ketenyl anion

A ketenyl anion contains a C=C=O allene-like functional group, similar to ketene, with a negative charge on either terminal carbon or oxygen atom, forming resonance structures by moving a lone pair of electrons on C-C-O bond. Ketenes have been sources for many organic compounds with its reactivity despite a challenge to isolate them as crystal. Precedent method to obtain this product has been at gas phase or at reactive intermediate, and synthesis of ketene is used be done in extreme conditions. Recently found stabilized ketenyl anions become easier to prepare compared to precedent synthetic procedure. A major feature about stabilized ketene is that it can be prepared from carbon monoxide (CO) reacting with main-group starting materials such as ylides, silylene, and phosphinidene to synthesize and isolate for further steps. As CO becomes a more common carbon source for various type of synthesis, this recent finding about stabilizing ketene with main-group elements opens a variety of synthetic routes to target desired products.

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