Photolysis of diazomethane to produce a carbene

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

Carbenes are neutral species containing a carbon atom with only six valence electrons. They can be produced when light energy promotes the loss of nitrogen from the diazomethane molecule without protonation, leaving behind a carbon atom with just two hydrogen bonds and only six electrons (two in each bond and two non-bonding electrons).

Z. Zhang and J. Wang, Tetrahedron, 2008, 64, 6577–6605.