Dihydroimidazol-2-ylidene
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| Dihydroimidazol-2-ylidene | |
|---|---|
| File:Dihydroimidazol-2-ylidene.png | |
| Dihydroimidazol-2-ylidene | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| ChemSpider | 11350507 
|
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| InChI key | JKQUEGZDRZXJNY-UHFFFAOYSA-N |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C3H6N2 |
| Molar mass | 70.09 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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]
File:Wanzlick1.png
Wanzlick's mechanism for the reaction of dihydroimidazol-2-ylidene with electrophiles
File:Arduengo4.svg
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
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- ↑ 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.
