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.