Synthesis and rearrangement of diphosphorus analogues of amidinium salts

Kato T, Gornitzka H, Baceiredo A, Schoeller W, Bertrand G (2002)
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 124(11): 2506-2512.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Transient diphosphinocarbocations UP are generated either by addition of phosphenium salts to the stable [bis(diisopropylamino)phosphino](silyl)carbene or by chloride abstraction from C-phosphino-P-chloro phosphorus ylides. In contrast to their nitrogen anlogues (amidinium salts) IIN, which feature a planar 3-center-4p-electron system, calculations show that IIIp should exist as IIPb, in which one phosphorus is planar, while the other remains pyramidal. With small substituents at phosphorus, derivatives of type HIP rearrange by a 1,3-shift of a phosphorus substituent to the other phosphorus center to give C-phosphoniophosphaalkenes, When bulky substituents are present at phosphorus, derivatives IIP undergo ring closure, giving rise to the corresponding cyclic valence isomers HIP, in which the carbon atom bears a negative charge. Diphosphinocarbocations HIP can be trapped by acetonitrile giving regioselectively the corresponding [2 + 3] cycloadduct.
Erscheinungsjahr
Zeitschriftentitel
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Band
124
Zeitschriftennummer
11
Seite
2506-2512
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eISSN
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Kato T, Gornitzka H, Baceiredo A, Schoeller W, Bertrand G. Synthesis and rearrangement of diphosphorus analogues of amidinium salts. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. 2002;124(11):2506-2512.
Kato, T., Gornitzka, H., Baceiredo, A., Schoeller, W., & Bertrand, G. (2002). Synthesis and rearrangement of diphosphorus analogues of amidinium salts. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 124(11), 2506-2512. doi:10.1021/ja010347h
Kato, T., Gornitzka, H., Baceiredo, A., Schoeller, W., and Bertrand, G. (2002). Synthesis and rearrangement of diphosphorus analogues of amidinium salts. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 124, 2506-2512.
Kato, T., et al., 2002. Synthesis and rearrangement of diphosphorus analogues of amidinium salts. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 124(11), p 2506-2512.
T. Kato, et al., “Synthesis and rearrangement of diphosphorus analogues of amidinium salts”, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, 2002, pp. 2506-2512.
Kato, T., Gornitzka, H., Baceiredo, A., Schoeller, W., Bertrand, G.: Synthesis and rearrangement of diphosphorus analogues of amidinium salts. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. 124, 2506-2512 (2002).
Kato, T, Gornitzka, H, Baceiredo, A, Schoeller, Wolfgang, and Bertrand, G. “Synthesis and rearrangement of diphosphorus analogues of amidinium salts”. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 124.11 (2002): 2506-2512.

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
Cyclic carbodiphosphoranes: strongly nucleophilic sigma-donor ligands.
Marrot S, Kato T, Gornitzka H, Baceiredo A., Angew Chem Int Ed Engl 45(16), 2006
PMID: 16534821
A stable P-heterocyclic carbene.
Martin D, Baceiredo A, Gornitzka H, Schoeller WW, Bertrand G., Angew Chem Int Ed Engl 44(11), 2005
PMID: 15712311

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