Dihydroimidazol-2-ylidene

Dihydroimidazol-2-ylidene is a hypothetical organic compound with formula C3H6N2.

It would be a heterocyclic compound, formally derived from imidazolidine with two hydrogen atoms removed from carbon number 2, leaving two vacant chemical bonds — which makes it a carbene.

Although carbenes in general are extremely short-lived, some derivatives of this compound are surprisingly stable, and form an important class of the persistent carbenes.

They include the first stable carbenes postulated (but not isolated) by Hans-Werner Wanzlick around 1960.

[1][2][3] They also include an example of the (saturated) imidazolin-2-ylidene (carbene) reported by A.J.

Skeletal formula of dihydroimidazol-2-ylidene
Skeletal formula of dihydroimidazol-2-ylidene
Wanzlick's mechanism for the reaction of dihydroimidazol-2-ylidene with electrophiles
1,3-Dimesityl-imidazol-4,5-dihydro-2-ylidene , a stable carbene without delocalization around the ring containing the carbenic carbon
( external viewer )