A Crystalline Phosphinyl Radical Cation

作者: Olivier Back , Mehmet Ali Celik , Gernot Frenking , Mohand Melaimi , Bruno Donnadieu

DOI: 10.1021/JA1046846

关键词: AlkylSubstituentCarbenePolymer chemistryPhosphaalkeneChemistryRadical ionSolid-statePhotochemistryCationic polymerization

摘要: One-electron oxidation of a readily available phosphaalkene derived from cyclic (alkyl)(amino)carbene affords phosphorus-centered radical cation that is indefinitely stable both in solution and the solid state, allowing single X-ray diffraction study to be performed. This species can regarded as phosphinyl bearing cationic substituent or, alternatively, carbene-stabilized phospheniumyl (carbene−RP+•).

参考文章(33)
Bassirou Ndiaye, Shrinivasa Bhat, Abdelaziz Jouaiti, Théo Berclaz, Gérald Bernardinelli, Michel Geoffroy, EPR and DFT studies of the structure of phosphinyl radicals complexed by a pentacarbonyl transition metal. Journal of Physical Chemistry A. ,vol. 110, pp. 9736- 9742 ,(2006) , 10.1021/JP061960W
Takeshi Matsumoto, François P. Gabbaï, A Borenium Cation Stabilized by an N-Heterocyclic Carbene Ligand Organometallics. ,vol. 28, pp. 4252- 4253 ,(2009) , 10.1021/OM900476G
Y. Wang, Y. Xie, P. Wei, R. B. King, H. F. Schaefer, P. von R. Schleyer, G. H. Robinson, A stable silicon(0) compound with a Si=Si double bond. Science. ,vol. 321, pp. 1069- 1071 ,(2008) , 10.1126/SCIENCE.1160768
Shigekazu Ito, Manabu Kikuchi, Masaaki Yoshifuji, Anthony J. Arduengo, Tatyana A. Konovalova, Lowell D. Kispert, Preparation and characterization of an air-tolerant 1,3-diphosphacyclobuten-4-yl radical. Angewandte Chemie. ,vol. 45, pp. 4341- 4345 ,(2006) , 10.1002/ANIE.200600950
Shigeru Sasaki, Fumiki Murakami, Masaaki Yoshifuji, Synthesis, Structure, and Radical Anion of the First Stablep-Phosphaquinone Angewandte Chemie International Edition. ,vol. 38, pp. 340- 343 ,(1999) , 10.1002/(SICI)1521-3773(19990201)38:3<340::AID-ANIE340>3.0.CO;2-8
Manfred Scheer, Christian Kuntz, Markus Stubenhofer, Michael Linseis, Rainer F. Winter, Marek Sierka, The complexed triphosphaallyl radical, cation, and anion family. Angewandte Chemie. ,vol. 48, pp. 2600- 2604 ,(2009) , 10.1002/ANIE.200805892
John C. Walton, Malika Makhlouf Brahmi, Louis Fensterbank, Emmanuel Lacôte, Max Malacria, Qianli Chu, Shau-Hua Ueng, Andrey Solovyev, Dennis P. Curran, EPR Studies of the Generation, Structure, and Reactivity of N-Heterocyclic Carbene Borane Radicals Journal of the American Chemical Society. ,vol. 132, pp. 2350- 2358 ,(2010) , 10.1021/JA909502Q
Alan E. Reed, Larry A. Curtiss, Frank Weinhold, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chemical Reviews. ,vol. 88, pp. 899- 926 ,(1988) , 10.1021/CR00088A005
Yuzhong Wang, Yaoming Xie, Pingrong Wei, R. Bruce King, Henry F. Schaefer, Paul v. R. Schleyer, Gregory H. Robinson, Carbene-stabilized diphosphorus. Journal of the American Chemical Society. ,vol. 130, pp. 14970- 14971 ,(2008) , 10.1021/JA807828T
Shau-Hua Ueng, Andrey Solovyev, Xinting Yuan, Steven J. Geib, Louis Fensterbank, Emmanuel Lacôte, Max Malacria, Martin Newcomb, John C. Walton, Dennis P. Curran, N-Heterocyclic Carbene Boryl Radicals: A New Class of Boron-Centered Radical Journal of the American Chemical Society. ,vol. 131, pp. 11256- 11262 ,(2009) , 10.1021/JA904103X