Chemie polyfunktioneller Liganden. 71. Darstellung und spektroskopische Charakterisierung von drei Bis(diphenylmethylphosphin)iminium‐Salzen, sowie spektroskopischer Vergleich mit dem isomeren [(Diphenylphosphin‐N‐methyl‐amino)diphenyl‐methyl‐phosphonium]‐iodid

Ellermann, Jochen; Lietz, Martin; Geibel, Kurt

doi:10.1002/zaac.19824920114

Cited by 12 publications

(1 citation statement)

References 16 publications

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“…32 It is interesting to note that treatment of 1 with KH and MeI only gave the phosphorus ylide derivative 2 (Scheme 1), a similar observation was reported for the alkylation of dppa (Ph 2 PNHPPh 2 ). 33 The hemilabile properties of 1 and 3 were evidenced by their dynamic behaviour in complexes 4 and 12a and in complex 15, respectively. Yet, the situation in 4 was quite unexpected, since it has been observed that the reaction of [Pd(dmba)(µ-Cl)] 2 with P,O phosphines, such as Ph 2 PCH 2 C(O)R (R = Ph, NPh 2 , etc.…”

Section: Discussionmentioning

confidence: 99%

Coordination properties of novel hemilabile acetamide-derived P,O phosphine ligands. Crystal structures of Ph2PNHC(O)Me and [PdMe{PPh2NHC(O)Me}{PPh2NHC(O)Me}][O3SCF3] †

Braunstein

Frison

Morise

et al. 2000

J. Chem. Soc., Dalton Trans.

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Cationic methyl Pd() complexes are described in which the new heterofunctional phosphine ligands Ph 2 PNHC(O)Me 1 or Ph 2 PN(Me)C(O)Me 3 behave as rigid and/or hemilabile P,O chelates. The chelating ability of 3 is higher than that of 1 and both are compared to that of other P,O ligands, such as the keto-and amido-phosphines Ph 2 PCH 2 C(O)Ph and Ph 2 PCH 2 C(O)NPh 2 , respectively. The crystal structure of 1 reveals the presence in the solid-state of an intermolecular hydrogen-bonded network N-H ؒ ؒ ؒ O and that of12b establishes the presence of both a chelating and a monodentate ligand 1 in the same complex. Carbonylation of the cationic methyl complexes 8a, 17, 18a and 20a afforded the corresponding acetyl complexes in which this ligand occupies a position cis to phosphorus, irrespective of that of the alkyl ligand in the precursor complex.

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Section: Discussionmentioning

confidence: 99%

Coordination properties of novel hemilabile acetamide-derived P,O phosphine ligands. Crystal structures of Ph2PNHC(O)Me and [PdMe{PPh2NHC(O)Me}{PPh2NHC(O)Me}][O3SCF3] †

Braunstein

Frison

Morise

et al. 2000

J. Chem. Soc., Dalton Trans.

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ChemInform Abstract: CHEMISTRY OF POLYFUNCTIONAL LIGANDS. 71. PREPARATION AND SPECTROSCOPIC CHARACTERIZATION OF THREE BIS(DIPHENYLMETHYLPHOSPHINE)IMINIUM SALTS, AS WELL AS A SPECTROSCOPIC COMPARISON WITH THE ISOMERIC ((DIPHENYLPHOSPHINE‐N‐METHYLAMINO)DIPHENYLMETHYLPHOSPHONIUM) IODIDE

Ellermann¹,

Lietz²,

Geibel³

1983

Chemischer Informationsdienst

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Chemie polyfunktioneller Moleküle. 101 [1]: Synthese eines Diphenylphosphin‐substituierten Cyclophosphamide und Röntgenstrukturanalyse seines Oxidations‐produkts

Ellermann

Knoch

Moll

et al. 1989

Zeitschrift anorg allge chemie

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Inhaltsübersicht. Diphenylphosphin und rac‐Cyclophosphamid (ClCH2CH2)2NP(O)N(H)(CH2)3O (1) reagieren in Gegenwart von n‐Butyllithium zu einem Zwischenprodukt, das mit Wasser das diphenylphosphinsubstituierte Cyclophosphamid, (Ph2PCH2CH2)2NP(O)N(H)(CH2)3O, (2) bildet. Metallierung von 2 mit n‐BuLi am N(3)‐Atom und Umsetzung mit D2O führt zum N(3)‐Deuteroderivat 2a. Mit H2O2 reagiert 2 zur all‐Phosphinoxid Verbindung, [Ph2P(O)CH2CH2]2NP(O)N(H)(CH2)3O, (4), die mit 0,5 Mol Wasser auskristallisiert und von der zur Charakterisierung des H‐Bückenbindungssystems eine Röntgenstrukturanalyse angefertigt wurde. Die NMR‐Spektren (1H, 13C, 31P, 14N) weisen 2–4 als dynamische Moleküle aus. Chemistry of Polyfunctional Molecules. 101. Synthesis of a Diphenylphosphinesubstituted Cyclophosphamide and the X‐ray Diffraction of its Oxidation Product Diphenylphosphine and rac‐cyclophosphamide, (ClCH2CH2)2NP(O)N(H)(CH2)3O, (1) react in the presence of n‐BuLi to an intermediate which hydrolyses to the diphenylphosphine substituted Cyclophosphamide, (Ph2PCH3CH2)2NP(O)N(H)(CH2)3O, (2). Metallation of 2 with n‐BuLi at the N(3) atom, followed by treatment with D2O yields the N(3)‐deuterated derivative 2a. With H2O2 2 forms the all‐phosphine‐oxide compound, [Ph2P(O)CH2CH2]2NP(O)N(H)(CH2)3O, (4), which crystallizes with 0.5 mole of water. In order to characterize the H‐bridge bonding system a X‐ray structure analysis of 4 was carried out. The NMR‐Spectra (1H, 13C, 31P, 14N) indicate 2–4 as dynamic molecules.

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Chemie polyfunktioneller Liganden. 71. Darstellung und spektroskopische Charakterisierung von drei Bis(diphenylmethylphosphin)iminium‐Salzen, sowie spektroskopischer Vergleich mit dem isomeren [(Diphenylphosphin‐N‐methyl‐amino)diphenyl‐methyl‐phosphonium]‐iodid

Cited by 12 publications

References 16 publications

Coordination properties of novel hemilabile acetamide-derived P,O phosphine ligands. Crystal structures of Ph2PNHC(O)Me and [PdMe{PPh2NHC(O)Me}{PPh2NHC(O)Me}][O3SCF3] †

Coordination properties of novel hemilabile acetamide-derived P,O phosphine ligands. Crystal structures of Ph2PNHC(O)Me and [PdMe{PPh2NHC(O)Me}{PPh2NHC(O)Me}][O3SCF3] †

ChemInform Abstract: CHEMISTRY OF POLYFUNCTIONAL LIGANDS. 71. PREPARATION AND SPECTROSCOPIC CHARACTERIZATION OF THREE BIS(DIPHENYLMETHYLPHOSPHINE)IMINIUM SALTS, AS WELL AS A SPECTROSCOPIC COMPARISON WITH THE ISOMERIC ((DIPHENYLPHOSPHINE‐N‐METHYLAMINO)DIPHENYLMETHYLPHOSPHONIUM) IODIDE

Chemie polyfunktioneller Moleküle. 101 [1]: Synthese eines Diphenylphosphin‐substituierten Cyclophosphamide und Röntgenstrukturanalyse seines Oxidations‐produkts

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