 | It has been suggested that this article be split into a new article titled Transition metal phosphinidine complex. (discuss) (December 2024) |
Phosphinidenes (IUPAC: phosphanylidenes, formerly phosphinediyls) are low-valent phosphorus compounds analogous to carbenes and nitrenes, having the general structure RP.[1][2] The parent phosphinidine has the formula PH. More common are the organic analogues where R = alkyl or aryl. In these compounds phosphorus has only 6 electrons in its valence level.[2] Most phosphinidenes are highly reactive and short-lived, thereby complicating empirical studies on their chemical properties.[3][4]
A variety of strategies have been employed to stabilize phosphinidenes (e.g. π-donation, steric protection, transition metal complexation),[2][3] Furthermore reagents and systems have been developed that can generate and transfer phosphinidenes as intermediates in the synthesis of various organophosphorus compounds.[5][6][7][8]
- ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "phosphanylidenes". doi:10.1351/goldbook.P04549
- ^ a b c Lammertsma, Koop (2003), Majoral, Jean-Pierre (ed.), "Phosphinidenes", New Aspects in Phosphorus Chemistry III, Topics in Current Chemistry, vol. 229, Berlin, Heidelberg: Springer, pp. 95–119, doi:10.1007/b11152, ISBN 978-3-540-36551-8, retrieved 2020-11-02
- ^ a b Liu, Liu; Ruiz, David A.; Munz, Dominik; Bertrand, Guy (2016). "A Singlet Phosphinidene Stable at Room Temperature". Chem. 1: 147-153. doi:10.1016/j.chempr.2016.04.001.
- ^ Nguyen, Minh Tho; Van Keer, Annik; Vanquickenborne, Luc G. (1996). "In Search of Singlet Phosphinidenes". The Journal of Organic Chemistry. 61 (20): 7077–7084. doi:10.1021/jo9604393. ISSN 0022-3263. PMID 11667609.
- ^ Transue, Wesley J.; Velian, Alexandra; Nava, Matthew; García-Iriepa, Cristina; Temprado, Manuel; Cummins, Christopher C. (2017-08-09). "Mechanism and Scope of Phosphinidene Transfer from Dibenzo-7-phosphanorbornadiene Compounds". Journal of the American Chemical Society. 139 (31): 10822–10831. doi:10.1021/jacs.7b05464. hdl:1721.1/117205. ISSN 0002-7863. PMID 28703579.
- ^ Hansen, Kerstin; Szilvási, Tibor; Blom, Burgert; Inoue, Shigeyoshi; Epping, Jan; Driess, Matthias (2013-08-14). "A Fragile Zwitterionic Phosphasilene as a Transfer Agent of the Elusive Parent Phosphinidene (:PH)". Journal of the American Chemical Society. 135 (32): 11795–11798. doi:10.1021/ja4072699. ISSN 0002-7863. PMID 23895437.
- ^ Krachko, Tetiana; Bispinghoff, Mark; Tondreau, Aaron M.; Stein, Daniel; Baker, Matthew; Ehlers, Andreas W.; Slootweg, J. Chris; Grützmacher, Hansjörg (2017). "Facile Phenylphosphinidene Transfer Reactions from Carbene–Phosphinidene Zinc Complexes". Angewandte Chemie International Edition. 56 (27): 7948–7951. doi:10.1002/anie.201703672. hdl:11245.1/4fe684ed-b624-415c-8873-4a6e9114f66b. ISSN 1521-3773. PMID 28505382.
- ^ Pagano, Justin K.; Ackley, Brandon J.; Waterman, Rory (2018-02-21). "Evidence for Iron-Catalyzed α-Phosphinidene Elimination with Phenylphosphine". Chemistry – A European Journal. 24 (11): 2554–2557. doi:10.1002/chem.201704954. ISSN 0947-6539. PMID 29194820.