A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations

Kato T, Gornitzka H, Baceiredo A, Schoeller W, Bertrand G (2000)
SCIENCE 289(5480): 754-756.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Diaminocarbocations (or amidinium salts) feature a three-center 4 pi electron system with an open planar structure. Their 2 pi electron three-membered cyclic valence isomers, in which the carbon atom bears a negative charge, are predicted to be about 541 kilojoules per mate higher in energy than the open form. This isomer has not been identified yet. In contrast, the attempted synthesis of a diphosphorus analog of amidinium salts Leads to the cyclic carbanionic form. There is no precedent for such a transformation of a carbocationic center into a carbanionic center, but with the help of heavier main-group elements, numerous examples can be imagined. This approach will enable the preparation of many unknown structural moieties that are difficult or even impossible to access in the corresponding carbon and nitrogen series.
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SCIENCE
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289
Zeitschriftennummer
5480
Seite
754-756
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Kato T, Gornitzka H, Baceiredo A, Schoeller W, Bertrand G. A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations. SCIENCE. 2000;289(5480):754-756.
Kato, T., Gornitzka, H., Baceiredo, A., Schoeller, W., & Bertrand, G. (2000). A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations. SCIENCE, 289(5480), 754-756. doi:10.1126/science.289.5480.754
Kato, T., Gornitzka, H., Baceiredo, A., Schoeller, W., and Bertrand, G. (2000). A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations. SCIENCE 289, 754-756.
Kato, T., et al., 2000. A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations. SCIENCE, 289(5480), p 754-756.
T. Kato, et al., “A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations”, SCIENCE, vol. 289, 2000, pp. 754-756.
Kato, T., Gornitzka, H., Baceiredo, A., Schoeller, W., Bertrand, G.: A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations. SCIENCE. 289, 754-756 (2000).
Kato, T, Gornitzka, H, Baceiredo, A, Schoeller, Wolfgang, and Bertrand, G. “A cyclic carbanionic valence isomer of a carbocation: Diphosphino analogs of diaminocarbocations”. SCIENCE 289.5480 (2000): 754-756.

4 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Phospha-organic chemistry: from molecules to polymers.
Bates JI, Dugal-Tessier J, Gates DP., Dalton Trans 39(13), 2010
PMID: 20449439
Stable cyclic carbenes and related species beyond diaminocarbenes.
Melaimi M, Soleilhavoup M, Bertrand G., Angew Chem Int Ed Engl 49(47), 2010
PMID: 20836099
Cyclic bis(phosphanyl)carbenium ion by protonation of a 1,3-diphosphacyclobutane-2,4-diyl.
Sebastian M, Hoskin A, Nieger M, Nyulászi L, Niecke E., Angew Chem Int Ed Engl 44(9), 2005
PMID: 15674990

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