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Original Articles

Isomerization and application of phospholene oxides

, , , , &
Pages 610-613 | Received 28 Sep 2018, Accepted 24 Nov 2018, Published online: 30 Dec 2018

References

  • Kollár, L.; Keglevich, G. P-heterocycles as Ligands in Homogeneous Catalytic Reactions. Chem. Rev. 2010, 110, 4257–4302.
  • Quin, L. D.; . Barket, T. P. Structure of Isoprene-Phenylphosphonous Dihalide Cyclo-adducts. Chem. Commun. 1967, 18, 914–915. DOI:10.1039/C19670000914.
  • Hunger, K.; Hasserodt, U.; Korte, F. Phospholin-derivate—II. Tetrahedron 1964, 20, 1593–1604. DOI:10.1016/S0040-4020(01)99156-2.
  • Pav, O.; Zbornikova, E.; Budensinsky, M.; Rosenberg, I. A New Class of Phosphanucleosides Containing a 3-hydroxy-1-hydroxymethylphospholane 1-oxide Ring. Tetrahedron 2013, 69, 9120–9129. DOI:10.1016/j.tet.2013.08.021.
  • Montchamp, J.-L.; Tian, F.; Frost, J. W. Double Arbuzov Reaction of in Situ Generated Bis(trimethylsiloxy)phosphine with Dielectrophiles: Methodology for the Synthesis of Cyclic Phosphinic Acids. J. Org. Chem. 1995, 60, 6076–6681. DOI:10.1021/jo00124a018.
  • Bujard, M.; Gouverneur, V.; Mioskowski, C. A Highly Efficient and Practical Synthesis of Cyclic Phosphinates Using Ring-Closing Metathesis. J. Org. Chem. 1999, 64, 2119–2123.
  • Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Improvement in Olefin Metathesis Using a New Generation of Ruthenium Catalyst Bearing an Imidazolylidene Ligand: synthesis of Heterocycles. Org. Lett. 2000, 2, 1517–1519.
  • Quin, L. D.; Gratz, J. P.; Barket, T. P. Structure of Diene-phosphonous Dihalide Addition Products and of Derived Phospholenes and Phospholene Oxides. J. Org. Chem. 1968, 33, 1034–1041.
  • Fujie, M.; Nakamura, S.; Asai, K.; Niimi, T.; Yamashita, J.; Kiyofuji, K.; Shibata, K.; Suzuki, M.; Aoshima, R.; Urano, T.; et al. A Novel Phospha Sugar Analogue: Synthesis and Evaluation of 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide as a New Class of Potential Anti-Proliferative Materials for Leukemia Cells. Heterocycl. Commun. 2009, 15, 273–278.
  • Yamashita, M.; Iida, A.; Mizuno, H.; Miyamoto, Y.; Morishita, T.; Sata, N.; Kiguchi, K.; Yabui, A.; Oshikawa, T. Reactions of 2-phospholene 1-oxides with Bromine in Some Media: Facile Preparation of Bromohydrin Derivatives of 2-Phospholenes. Heteroat. Chem. 1993, 4, 553–557. DOI:10.1002/hc.520040606.
  • Yamashita, M.; Reddy, V. K.; Rao, L. N.; Haritha, B.; Maeda, M.; Suzuki, K.; Totsuka, H.; Takahashi, M.; Oshikawa, T. An Efficient Approach towards the Stereospecific Synthesis of Epoxides from Phospholene Oxides. Tetrahedron Lett. 2003, 44, 2339–2341. DOI:10.1016/S0040-4039(03)00255-7.
  • Bálint, E.; Jablonkai, E.; Bálint, M.; Keglevich, G. Alkylating Esterification of 1‐hydroxy‐3‐phospholene Oxides Under Solventless MW Conditions. Heteroatom Chem. 2010, 21, 211–214.
  • Kiss, N. Z.; Ludányi, K.; Drahos, L.; Keglevich, G. Novel Synthesis of Phosphinates by the Microwave-Assisted Esterification of Phosphinic Acids. Synt. Commun. 2009, 39, 2392–2404. DOI:10.1080/00397910802654880.
  • Keglevich, G.; Rádai, Z.; Harsági, N.; Szigetvári, Á.; Kiss, N. Z. A Study on the Acidic Hydrolysis of Cyclic Phosphinates: 1-Alkoxy-3-phospholene 1-oxides, 1-ethoxy-3-methylphospholane 1-oxide, and 1-ethoxy-3-methyl-1,2,3,4,5,6-hexahydrophosphinine 1-Oxide. Heteroatom Chem. 2017, 28, e21394. DOI:10.1002/hc.21394.
  • Herbay, R.; Bagi, P.; Mucsi, Z.; Mátravölgyi, B.; Drahos, L.; Fogassy, E.; Keglevich, G. A Novel Preparation of Chlorophospholenium Chlorides and Their Application in the Synthesis of Phospholene Boranes. Tetrahedron Lett. 2017, 58, 458–461. DOI:10.1016/j.tetlet.2016.12.059.
  • Keglevich, G.; Kollár, L. Platinum Complexes of Five- and Six-Membered P-Heterocycles as Potential Catalysts. Lett. Org. Chem. 2010, 7, 612–620. DOI:10.2174/157017810793811713.
  • Bagi, P.; Kovács, T.; Szilvási, T.; Pongrácz, P.; Kollár, L.; Drahos, L.; Fogassy, E.; Keglevich, G. Platinum(II) complexes Incorporating Racemic and Optically Active 1-alkyl-3-phospholene P-ligands: Synthesis, Stereostructure, NMR Properties and Catalytic Activity. J. Organomet. Chem. 2014, 751, 306–313. DOI:10.1016/j.jorganchem.2013.03.045.
  • Bagi, P.; Szilvási, T.; Pongrácz, P.; Kollár, L.; Drahos, L.; Keglevich, G. Platinum(II) Complexes Incorporating Racemic and Optically Active 1-Aryl-3- phospholene P-Ligands as Potential Catalysts in Hydroformylation. Curr. Org. Chem. 2014, 18, 1529–1538. DOI:10.2174/1385272819666140609224751.

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