Home Wasserlösliche Phosohane, XIV. Hydrophile Derivate des Triphenylphosphans mit NH2-, COOH- und P(O)(OR)2-funktionalisierten Seitenketten / Water Soluble Phosphanes, XIV. Hydrophilic Derivatives of Triphenylphosphane with NH2, COOH and P (O)(OR)2 Functionalized Side Chains
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Wasserlösliche Phosohane, XIV. Hydrophile Derivate des Triphenylphosphans mit NH2-, COOH- und P(O)(OR)2-funktionalisierten Seitenketten / Water Soluble Phosphanes, XIV. Hydrophilic Derivatives of Triphenylphosphane with NH2, COOH and P (O)(OR)2 Functionalized Side Chains

  • Christian Liek , Peter Machnitzki , Thomas Nickel , Stefan Schenk , Michael Tepper and Othmar Stelzer
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 54 Issue 12

Nucleophilic phosphanylation of ortho-fluorophenylacetic acid or ortho-fluorobenzylamine with PhPH2 using KOtBu as the base affords the hydrophilic tertiary phosphanes 3 and 4a with terminal CH2-COOH and CH2-NH2 substituents. The corresponding secondary phosphane ligands 2 or 5 may be obtained by Pd-catalyzed P-C coupling of ortho-iodophenylacetic acid with PhPH2 or selective nucleophilic phosphanylation of ortho-fluorophenylacetic acid. Novel phosphonatomethyl derivatives 7a, 7b of triphenylphosphane have been obtained in a two stage synthesis using ortho-iodobenzylchloride or meta-iodobenzylbromide as starting materials. Arbusov reaction with P(OEt)3 and Pd-catalyzed P-C coupling reactions with Ph2PH gave the esters 7a, 7b. Purification of 7a was achieved via its BH3 adduct 8a. Deprotection, hydrolysis and neutralisation with NaOH affords the water soluble sodium salts 9a,9b. α-Hydroxy and α-benzylamino derivatives 12 and 14 of ortho-diphenylphosphanobenzyl phosphonate (e.g. 7a) and the corresponding Me2P(O) analogs 13 and 16 are accessible in a straightforward manner by addition of (MeO)2P(O)H or Me2P(O)H to ortho-phosphanobenzaldehyde 11a or its benzaldimino derivative 15, respectively. An improved synthesis for 11a -11c has been developed. Reaction of 11a with the Wittig reagent Ph3P=C(H)COOEt and subsequent hydrolysis of the intermediate ester 17a affords ortho-diphenylphosphano cinnamic acid 17. The catalytical activity of 1,9a, 9b and related ligands in Suzuki-type coupling reactions has been investigated.

Keywords : Aminomethyl; Carboxymethyl; Phosphanomethyl Derivatives; α-Amino- and α-Hydroxymethyl Phosphonic Acid and Phosphane Oxide Derivatives; 2-Diphenylphosphano Cinnamic Acid
Received: 1999-7-7
Published Online: 2014-6-2
Published in Print: 1999-12-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Preparation and Crystal Structure of the Calcium Rhenate(VI, VII) Ca5Re3O15-x
  2. The Silver(I) Mercury(II) Oxide Nitrate with the Empirical Formula AgHg2NO5
  3. A Simple and Convenient Route to Arylxenon(II) Tetrafluoroborates
  4. New Chalcogenogermanates with Adamantane Type Complex Anions: Preparation and Crystal Structures of K4Ge4S10; Rb4Ge4S10, Rb4Ge4Se10, and Cs4Ge4Se10
  5. Neue Chalkogenometallate mit binuklearen Anionen, I: Darstellung und Kristallstruktur von Rb6Sn2S7 / New Chalcogenometallates with Binuclear Anions, I: Preparation and Crystal Structure of Rb6Sn2S7
  6. Three-dimensional Copper(I) Halide Based Coordination Networks with Asymmetrically Substituted Bridging N-Donor Ligands
  7. Equilibrium and Structural Study of Chloro Complexes of Iron(III) Ion in Acidic Aqueous Solution by Means of X-Ray Absorption Spectroscopy
  8. (CH3NH3)2Sb2S4, a New Thioantimonate(III) with Building Groups Stabilized by Hydrogen Bonds
  9. The Molecular and Electronic Structure of Tris(dimethylarsino)amine (Me2As)3N
  10. Wasserlösliche Phosohane, XIV. Hydrophile Derivate des Triphenylphosphans mit NH2-, COOH- und P(O)(OR)2-funktionalisierten Seitenketten / Water Soluble Phosphanes, XIV. Hydrophilic Derivatives of Triphenylphosphane with NH2, COOH and P (O)(OR)2 Functionalized Side Chains
  11. Aminocyclophosphazene Derivatives of Tungsten Carbonyl
  12. Darstellung von phosphorylierten Glucosiden durch Umsetzung am Glucosegerüst sowie am Aglycon / Synthesis of Phosphorylated Glucosides through Reaction at the Glucose Framework and at the Aglycon
  13. Schiff Bases of Methanesulfonylhydrazine. Synthesis, Spectroscopic Characterization, Conformational Analysis, and Biological Activity
  14. Zirconium Reagents for Organometallic Synthesis. Crystal Structures of ZrCl4 ·2Et2O and (Et2N)ZrCl3·Et2O
  15. Nitriles in Heterocyclic Organic Synthesis: Synthesis of Pyrano[2,3-h]coumarines, Pyrano[3,2-c]coumarines, and their Derivatives
  16. Redox Properties of 1,2-Dihydro[60]fullerene Derivatives with Electron-Withdrawing Substituents
  17. Chinazolinderivate durch Cyclodehydrierung von N-(2-substituierten Aryl)-Piperidinen / Quinazoline Derivatives by Cyclodehydrogenation of N-(2-Substituted Aryl)-Piperidines
  18. Reactions of Cyanothioacetamide Derivatives with 2-Hydrazinothiazol-4(5H)-one: Synthesis, Cyclization and Biological Evaluation of Several New Annelated Pyran, Thiazole, 1,2,4-Triazole and 1,2,4-Triazine Derivatives
  19. Structure of the 2-Pyrrolidinone Monohydrate
  20. X-Ray Structure Analysis of Substituted 5-(2,3-Dihydro-7-benzofuryl)- 1-methylpyrazolo[4,3-d]pyrimidin-7-one (Biagra)
  21. Coordination of the Hetero(N,S)- bidentate Ligand 1-Methyl-2- (methylthiomethyl)-1H-benzimidazole to [(Ph3P)Au)]+ Exclusively through the Imine Nitrogen Donor
  22. Die Kristallstruktur von [YbCl2(THF)5]+[WOCl4(THF)]- / Crystal Structure of [YbCl2(THF)5]+[WOCl4(THF)]-
  23. Die Kristallstrukturen von Ph3AsCI2 und β-Ph3AsBr2 / Crystal Structures of Ph3AsCI2 and β-Ph3AsBr2
  24. Neuuntersuchung der Kristallstruktur von α-ICl / Novel Investigation on the Crystal Structure of α-ICl
  25. A Facile Synthesis of Quino[2,3-a]carbazoles
  26. Subject Index
  27. Authors Index / Autorenverzeichnis
https://doi.org/10.1515/znb-1999-1210
Keywords for this article
Aminomethyl; Carboxymethyl; Phosphanomethyl Derivatives; α-Amino- and α-Hydroxymethyl Phosphonic Acid and Phosphane Oxide Derivatives; 2-Diphenylphosphano Cinnamic Acid

Articles in the same Issue

  1. Preparation and Crystal Structure of the Calcium Rhenate(VI, VII) Ca5Re3O15-x
  2. The Silver(I) Mercury(II) Oxide Nitrate with the Empirical Formula AgHg2NO5
  3. A Simple and Convenient Route to Arylxenon(II) Tetrafluoroborates
  4. New Chalcogenogermanates with Adamantane Type Complex Anions: Preparation and Crystal Structures of K4Ge4S10; Rb4Ge4S10, Rb4Ge4Se10, and Cs4Ge4Se10
  5. Neue Chalkogenometallate mit binuklearen Anionen, I: Darstellung und Kristallstruktur von Rb6Sn2S7 / New Chalcogenometallates with Binuclear Anions, I: Preparation and Crystal Structure of Rb6Sn2S7
  6. Three-dimensional Copper(I) Halide Based Coordination Networks with Asymmetrically Substituted Bridging N-Donor Ligands
  7. Equilibrium and Structural Study of Chloro Complexes of Iron(III) Ion in Acidic Aqueous Solution by Means of X-Ray Absorption Spectroscopy
  8. (CH3NH3)2Sb2S4, a New Thioantimonate(III) with Building Groups Stabilized by Hydrogen Bonds
  9. The Molecular and Electronic Structure of Tris(dimethylarsino)amine (Me2As)3N
  10. Wasserlösliche Phosohane, XIV. Hydrophile Derivate des Triphenylphosphans mit NH2-, COOH- und P(O)(OR)2-funktionalisierten Seitenketten / Water Soluble Phosphanes, XIV. Hydrophilic Derivatives of Triphenylphosphane with NH2, COOH and P (O)(OR)2 Functionalized Side Chains
  11. Aminocyclophosphazene Derivatives of Tungsten Carbonyl
  12. Darstellung von phosphorylierten Glucosiden durch Umsetzung am Glucosegerüst sowie am Aglycon / Synthesis of Phosphorylated Glucosides through Reaction at the Glucose Framework and at the Aglycon
  13. Schiff Bases of Methanesulfonylhydrazine. Synthesis, Spectroscopic Characterization, Conformational Analysis, and Biological Activity
  14. Zirconium Reagents for Organometallic Synthesis. Crystal Structures of ZrCl4 ·2Et2O and (Et2N)ZrCl3·Et2O
  15. Nitriles in Heterocyclic Organic Synthesis: Synthesis of Pyrano[2,3-h]coumarines, Pyrano[3,2-c]coumarines, and their Derivatives
  16. Redox Properties of 1,2-Dihydro[60]fullerene Derivatives with Electron-Withdrawing Substituents
  17. Chinazolinderivate durch Cyclodehydrierung von N-(2-substituierten Aryl)-Piperidinen / Quinazoline Derivatives by Cyclodehydrogenation of N-(2-Substituted Aryl)-Piperidines
  18. Reactions of Cyanothioacetamide Derivatives with 2-Hydrazinothiazol-4(5H)-one: Synthesis, Cyclization and Biological Evaluation of Several New Annelated Pyran, Thiazole, 1,2,4-Triazole and 1,2,4-Triazine Derivatives
  19. Structure of the 2-Pyrrolidinone Monohydrate
  20. X-Ray Structure Analysis of Substituted 5-(2,3-Dihydro-7-benzofuryl)- 1-methylpyrazolo[4,3-d]pyrimidin-7-one (Biagra)
  21. Coordination of the Hetero(N,S)- bidentate Ligand 1-Methyl-2- (methylthiomethyl)-1H-benzimidazole to [(Ph3P)Au)]+ Exclusively through the Imine Nitrogen Donor
  22. Die Kristallstruktur von [YbCl2(THF)5]+[WOCl4(THF)]- / Crystal Structure of [YbCl2(THF)5]+[WOCl4(THF)]-
  23. Die Kristallstrukturen von Ph3AsCI2 und β-Ph3AsBr2 / Crystal Structures of Ph3AsCI2 and β-Ph3AsBr2
  24. Neuuntersuchung der Kristallstruktur von α-ICl / Novel Investigation on the Crystal Structure of α-ICl
  25. A Facile Synthesis of Quino[2,3-a]carbazoles
  26. Subject Index
  27. Authors Index / Autorenverzeichnis
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