Dihydroimidazol-2-ylidene

Dihydroimidazol-2-ylidene
IUPAC name Dihydroimidazol-2-ylidene[citation needed]
Systematic name Imidazolidin-2-ylidene[citation needed]
Identifiers
ChemSpider	11350507 Y
Jmol-3D images	Image 1
SMILES [C]1NCCN1
InChI InChI=1S/C3H6N2/c1-2-5-3-4-1/h4-5H,1-2H2 Y Key: JKQUEGZDRZXJNY-UHFFFAOYSA-N Y InChI=1/C3H6N2/c1-2-5-3-4-1/h4-5H,1-2H2 Key: JKQUEGZDRZXJNY-UHFFFAOYAT
Properties
Molecular formula	C3N2H6
Molar mass	70.0931 g mol-1
Exact mass	70.053098202 g mol-1
Y (verify) (what is: Y/N?) 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 postulated (but not isolated) by Hans-Werner 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 delocalization around the ring.
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They also include an example of the (saturated) imidazolin-2-ylidene (carbene) reported by A.J. Arduengo in 1995.^[4]

References

1. ^ H.-W. Wanzlick and E. Schikora (1960). "Ein neuer Zugang zur Carben-Chemie". Angewandte Chemie 72 (14): 494. doi:10.1002/ange.19600721409. 
2. ^ H.-W. Wanzlick and E. Schikora (1960). "Ein nucleophiles Carben". Chemische Berichte 94 (9): 2389–2393. doi:10.1002/cber.19610940905. 
3. ^ H.-W. Wanzlick (1962). "Aspects of Nucleophilic Carbene Chemistry". Angew. Chem., Int. Ed. Engl. 1 (2): 75. doi:10.1002/anie.196200751. 
4. ^ A. J. Arduengo, III, H. V. R. Dias, R. L. Harlow, and M. Kline (1992). "Electronic stabilization of nucleophilic carbenes". J. Am. Chem. Soc. 114 (14): 5530. doi:10.1021/ja00040a007. 

This article about a heterocyclic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Carbenes Imidazolines Hypothetical chemical compounds Heterocyclic compound stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем решить контрольную работу Methyldihydromorphine Isocoumarin Look at other dictionaries: Persistent carbene — A stable carbene: isolated 1,3 dimesitylimidazol 2 ylidene in a Schlenk flask (stir bar also present). A persistent carbene (also known as stable carbene or Arduengo carbene) is a type of carbene demonstrating particular stability. The best known …   Wikipedia Grubbs' catalyst — is a transition metal carbene complex named after the chemist by whom it was first synthesized, Robert H. Grubbs. There are two generations of the catalyst, as shown on the right.Grubbs, R.H. [http://www.wiley… …   Wikipedia Grubbs-Katalysator — Der Grubbs Katalysator ist ein Ruthenium Carben Komplex der nach seinem Entdecker Robert H. Grubbs benannt wurde und in der Olefinmetathese Anwendung findet. Es gibt zwei Generationen des Katalysators.[1][2] Im Gegensatz zu anderen… …   Deutsch Wikipedia Grubbs-Katalysatoren — Der Grubbs Katalysator ist ein Ruthenium Carben Komplex, der nach seinem Entdecker Robert H. Grubbs benannt wurde und in der Olefinmetathese Anwendung findet. Es gibt zwei Generationen des Katalysators.[1][2] Im Gegensatz zu anderen… …   Deutsch Wikipedia Ring opening metathesis polymerisation — Ring opening metathesis polymerization (ROMP) is a type of olefin metathesis polymerization that produces industrially important products. The driving force of the reaction is relief of ring strain in cyclic olefins (e.g. norbornene or… …   Wikipedia Imidazoline — sind eine chemische Stoffgruppe aus dem Bereich der heterocyclischen Verbindungen und gehören zur Gruppe der Azoline. Ihre Mitglieder sind fünfgliedrige cyclische organische ungesättigte Verbindungen, die genau zwei nicht benachbarte… …   Deutsch Wikipedia Imidazolidine — Général Nom IUPAC imidazolidine Synonymes tétrahydro …   Wikipédia en Français Catalyseur de Grubbs — de 1re génération Général …   Wikipédia en Français 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”