Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory
Lavallo V, Canac Y, Donnadieu B, Schoeller W, Bertrand G (2006)
SCIENCE 312(5774): 722-724.
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Autor*in
Lavallo, V;
Canac, Y;
Donnadieu, B;
Schoeller, WolfgangUniBi;
Bertrand, G
Einrichtung
Abstract / Bemerkung
Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C3H2) has been presumed to be too unstable to isolate in the laboratory. However, by appending pi-electron-donating amino groups to the triangular skeleton, we prepared a cyclopropenylidene derivative that is stable at room temperature. In contrast to previously isolated carbenes, this compound does not require a heteroatom adjacent to the electron-deficient carbon to confer stability. Despite the presence of amino groups, the geometric parameters of the cyclic skeleton, revealed by x-ray crystallography, are only slightly perturbed relative to those of the calculated structure of unsubstituted cyclopropenylidene. Stable cyclopropenylidene derivatives might thus serve as models for a better understanding of the formation of carbon-bearing molecules in the interstellar medium.
Erscheinungsjahr
2006
Zeitschriftentitel
SCIENCE
Band
312
Ausgabe
5774
Seite(n)
722-724
ISSN
0036-8075
eISSN
1095-9203
Page URI
https://pub.uni-bielefeld.de/record/1599506
Zitieren
Lavallo V, Canac Y, Donnadieu B, Schoeller W, Bertrand G. Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory. SCIENCE. 2006;312(5774):722-724.
Lavallo, V., Canac, Y., Donnadieu, B., Schoeller, W., & Bertrand, G. (2006). Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory. SCIENCE, 312(5774), 722-724. https://doi.org/10.1126/science.1126675
Lavallo, V, Canac, Y, Donnadieu, B, Schoeller, Wolfgang, and Bertrand, G. 2006. “Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory”. SCIENCE 312 (5774): 722-724.
Lavallo, V., Canac, Y., Donnadieu, B., Schoeller, W., and Bertrand, G. (2006). Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory. SCIENCE 312, 722-724.
Lavallo, V., et al., 2006. Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory. SCIENCE, 312(5774), p 722-724.
V. Lavallo, et al., “Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory”, SCIENCE, vol. 312, 2006, pp. 722-724.
Lavallo, V., Canac, Y., Donnadieu, B., Schoeller, W., Bertrand, G.: Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory. SCIENCE. 312, 722-724 (2006).
Lavallo, V, Canac, Y, Donnadieu, B, Schoeller, Wolfgang, and Bertrand, G. “Cyclopropenylidenes: From interstellar space to an isolated derivative in the laboratory”. SCIENCE 312.5774 (2006): 722-724.
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Masuda JD, Martin D, Lyon-Saunier C, Baceiredo A, Gornitzka H, Donnadieu B, Bertrand G., Chem Asian J 2(1), 2007
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Recently reported crystalline isothiazole carbenes: myth or reality.
DeHope A, Lavallo V, Donnadieu B, Schoeller WW, Bertrand G., Angew Chem Int Ed Engl 46(36), 2007
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DeHope A, Lavallo V, Donnadieu B, Schoeller WW, Bertrand G., Angew Chem Int Ed Engl 46(36), 2007
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Cyclopropenylidene carbene ligands in palladium C-C coupling catalysis.
Wass DF, Haddow MF, Hey TW, Orpen AG, Russell CA, Wingad RL, Green M., Chem Commun (Camb) (26), 2007
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Wass DF, Haddow MF, Hey TW, Orpen AG, Russell CA, Wingad RL, Green M., Chem Commun (Camb) (26), 2007
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A stable chiral diaminocyclopropenylidene.
Holschumacher D, Hrib CG, Jones PG, Tamm M., Chem Commun (Camb) (35), 2007
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Holschumacher D, Hrib CG, Jones PG, Tamm M., Chem Commun (Camb) (35), 2007
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Stable four-pi-electron, four-membered heterocyclic cations and carbenes.
Ishida Y, Donnadieu B, Bertrand G., Proc Natl Acad Sci U S A 103(37), 2006
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Ishida Y, Donnadieu B, Bertrand G., Proc Natl Acad Sci U S A 103(37), 2006
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Isolation of cyclopropenylidene-lithium adducts: the Weiss-Yoshida reagent.
Lavallo V, Ishida Y, Donnadieu B, Bertrand G., Angew Chem Int Ed Engl 45(40), 2006
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Lavallo V, Ishida Y, Donnadieu B, Bertrand G., Angew Chem Int Ed Engl 45(40), 2006
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Carbon-carbon bond formation at a neutral terminal carbido ligand: generation of cyclopropenylidene and vinylidene complexes.
Caskey SR, Stewart MH, Johnson MJ, Kampf JW., Angew Chem Int Ed Engl 45(44), 2006
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