Dihydroimidazol-2-ylidene

Dihydroimidazol-2-ylidene
Names
	IUPAC name Dihydroimidazol-2-ylidene
	Systematic IUPAC name Imidazolidin-2-ylidene
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	11350507 ;
	InChI InChI=1S/C3H6N2/c1-2-5-3-4-1/h4-5H,1-2H2 Key: JKQUEGZDRZXJNY-UHFFFAOYSA-N ; InChI=1/C3H6N2/c1-2-5-3-4-1/h4-5H,1-2H2 Key: JKQUEGZDRZXJNY-UHFFFAOYAT;
	SMILES C1CN[C]N1;
Properties
Chemical formula	C3H6N2
Molar mass	70.095 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 obtained (but not isolated) by H. Wanzlick around 1960^[1]^[2]^[3]

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 the aromatic imidazolium ring.
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They include also the first example of a non-aromatic stable carbene isolated by A. Arduengo in 1995.^[4]

References

^ Hans-Werner Wanzlick and E. Schikora (1960). "Ein neuer Zugang zur Carben-Chemie". Angewandte Chemie. 72 (14): 494. doi:10.1002/ange.19600721409.
^ H. W. Wanzlick and E. Schikora (1960). "Ein nucleophiles Carben". Chemische Berichte. 94 (9): 2389–2393. doi:10.1002/cber.19610940905.
^ H. W. Wanzlick (1962). "Aspects of Nucleophilic Carbene Chemistry". Angew. Chem., Int. Ed. Engl. 1: 75. doi:10.1002/anie.196200751.
^ A. J. Arduengo, H. V. R. Dias, R. L. Harlow, and M. Kline (1992). "Electronic stabilization of nucleophilic carbenes". J. Am. Chem. Soc. 114: 5530. doi:10.1021/ja00040a007.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[Wanzlick1-1] Hans-Werner Wanzlick and E. Schikora (1960). "Ein neuer Zugang zur Carben-Chemie". Angewandte Chemie. 72 (14): 494. doi:10.1002/ange.19600721409.

[Wanzlick2-2] H. W. Wanzlick and E. Schikora (1960). "Ein nucleophiles Carben". Chemische Berichte. 94 (9): 2389–2393. doi:10.1002/cber.19610940905.

[Wanzlick3-3] H. W. Wanzlick (1962). "Aspects of Nucleophilic Carbene Chemistry". Angew. Chem., Int. Ed. Engl. 1: 75. doi:10.1002/anie.196200751.

[Arduengo2-4] A. J. Arduengo, H. V. R. Dias, R. L. Harlow, and M. Kline (1992). "Electronic stabilization of nucleophilic carbenes". J. Am. Chem. Soc. 114: 5530. doi:10.1021/ja00040a007.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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