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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Abstract
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.
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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.
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.
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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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