By Brian P. Johnson, Gabor Balazs, Manfred Scheer (auth.), Jean-Pierre Majoral (eds.)
B.P Johnson, G. Balazs, M. Scheer: Complexes with a Metal-Phosphorus Triple Bond.- M. Tanaka: Homogeneous Catalysis for H-P Bond Addition Reactions.- J.P. Dutasta: New Phosphorylated Hosts for the layout of recent Supramolecular Assemblies.- J. Michalski, W. Dabkowski: cutting-edge. Chemical Synthesis of Biophosphates and Their Analogues through PIII Derivatives.- A. Vioux, J. Le Bideau, P.H. Mutin, D. Leclercq: Hybrid Organic-Inorganic fabrics in line with Organophosphorus Derivatives.- D. Gudat: Zwitterionic Phospholide Derivatives-New Ambiphilic Ligands.- Y. Takagi, Y. Ikeda, ok. Taira: Ribozyme Mechanisms.
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Extra resources for New Aspects in Phosphorus Chemistry IV
2 Addition to Alkenes and Dienes Alkenes are much less reactive in the H-P bond addition reactions than alkynes. However, 1,3,2-dioxaphospholane 2-oxide (4a), a five-membered hydrogen phosphonate of pinacol, is exceptionally reactive with alkenes although dialkyl and diaryl phosphonates such as 4b–d are totally unreactive (Scheme 25) . Very interestingly, six-membered hydrogen phosphonates 4e,f are also unreactive under identical conditions. Scheme 25 As Scheme 26 demonstrates, the terminal alkene reactions using palladium-dppb [dppb=1,4-bis(diphenylphosphino)butane] catalyst systems usual- Scheme 26 42 Masato Tanaka ly form linear phosphonates with high regioselectivities.
The new procedures furnish allylic phosphonates of stereochemical integrity, and hence, the products are envisioned to allow numerous synthetic elaborations using Horner-Emmons olefination reactions. 1 Addition to Alkynes Addition of the H-P bond in secondary phosphine oxides (hydrophosphinylation) also proceeds in the presence of palladium complexes (Scheme 36) . Secondary phosphine oxides appear more reactive than hydrogen 46 Masato Tanaka phosphonates and the reaction proceeds even at room temperature.
On the basis of these results, it can be safely concluded that the rate-determining step is the reductive elimination process, which is the provenance of the significant reactivity difference depending on the structure of the alcohol moiety. Stockland and coworkers also studied the C-P(O) reductive elimination from (bipy)PdMe[P(O)(OPh)2] and related complexes to reconfirm the lack of the reactivity. However, when PPh3 was added, the complexes did reductively eliminate MeP(O)(OPh)2 . Scheme 31 44 Masato Tanaka The reason for the high reactivity of 13a is ambiguous.