Reactions of carbenes (O-H bond insertion)

NOTE: Important charges and non-bonding electrons are shown throughout the animation except during the transition phase

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Carbenes can insert into bonds such as O-H and N-H bonds. The mechanism involves addition of the oxygen lone pair into an empty p-orbital on the carbene, followed by proton transfer to generate a neutral molecule from the first formed zwitterion (or ylid).

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P. de Frémont, N. Marion and S. P. Nolan, Coord. Chem. Rev., 2009, 253, 862–892.

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