Synthesis and proton dissociation properties of arylphosphonates: A microwave-assisted catalytic arbuzov reaction with aryl bromides

Heteroatom Chemistry

Volumn 23, Issue 6, 2012, Pages 574-582

  Keglevich, György ^a   Grün, Alajos ^a   Bölcskei, Adrienn ^a   Drahos, László ^b   Kraszni, Márta ^c   Balogh, György T ^d  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c SEMMELWEIS UNIVERSITY   (Hungary)

^d GEDEON RICHTER LTD   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84869500046     PISSN: 10427163     EISSN: 10981071     Source Type: Journal    
DOI: 10.1002/hc.21053     Document Type: Article

References (54)

1. Quin L. D. A, Guide to Organophosphorus Chemistry; Wiley: New York, 2000.
2. Burger, A.; Dawson, N. D., J Org Chem 1951, 16, 1250-1254.
3. Kagayama, T.; Nakano, A.; Sakaguchi, S.; Ishii, Y., Org Lett 2006, 8, 407-409.
4. Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T., Tetrahedron Lett 1980, 21, 3595-3598.
5. Rao, H. H.; Jin, Y.; Fu, H.; Jiang, Y. Y., Zhao, Y. F., Chem Eur J 2006, 12, 3636-3646.
6. Huang, C.; Tang, X.; Fu, H.; Jiang, Y. Y., Zhao, Y. F., J Org Chem 2006, 71, 5020-5022.
7. Belabassi, Y.; Alzghari, S.; Montchamp, J.-L., J Organomet Chem 2008, 693, 3171-3178.
8. Deal, E. L.; Petit, C.; Montchamp, J.-L., Org Lett 2011, 13, 3270-3273.
9. Bessmerthnykh, A.; Douaihy, C. M.; Guilard, R., Chem Lett 2009, 38, 738-739.
10. Plumb, J. B.; Griffin, C. E., J Org Chem 1962, 27, 4711-4712.
11. Plumb, J. B.; Obrycki, R.; Griffin, C. E., J Org Chem 1966, 31, 2455-2458.
12. Obrycki, R.; Griffin, C. E., J Org Chem 1968, 33, 632-636.
13. Yuan, C.; Feng, H., Synthesis 1990, 140-141.
14. Villemin, D.; Elbilali, A.; Siméon, F.; Jaffrès, P.-A.; Maheut, G.; Mosaddak, M.; Hakiki, A., J Chem Res 2003, 436-437.
15. Guénin, E.; Meziane, D., Curr Org Chem 2011, 15, 3465-3485.
16. Keglevich, G.; Bálint, E.; Kiss, N. Z.; Jablonkai, E.; Hegedűs, L.; Grün, A.; Greiner, I., Curr Org Chem 2011, 15, 1802-1810.
17. Keglevich, G.; Kiss, N. Z.; Mucsi, Z.; Körtvélyesi, T., Org Biomol Chem 2012, 10, 2011-2018.
18. Keglevich, G.; Dudás, E., Synth Commun 2007, 37, 3191-3199.
19. Keglevich, G.; Forintos, H.; Körtvélyesi, T., Curr Org Chem 2004, 8, 1245-1261.
20. Keglevich G., Dudás E., Synth Commun 2007, 37, 3191-3199.
21. Keglevich, G.; Szekrényi, A., Lett Org Chem 2008, 5, 616-622.
22. Greiner, I.; Grün, A.; Ludányi, K.; Keglevich, G., Heteroatom Chem 2011, 22, 11-14.
23. Keglevich, G.; Grün, A.; Blastik, Z.; Greiner, I., Heteroatom Chem 2011, 22, 174-179.
24. Grün, A.; Blastik, Z.; Drahos, L.; Keglevich, G., Heteroatom Chem 2012, 23, 241-246.
25. Hansch, C.; Leo, A.; Taft, R. W., Chem Rev 1991, 91, 165-195.
26. Jaffe, H. H.; Freedman, L. D.; Doak, G. O., J Am Chem Soc 1954, 76, 1548-1552.
27. Nualláin, C. O., J Inorg Nucl Chem 1974, 36, 339-343.
28. Hoefnagel, A. J.; Hoefnagel, M. A.; Wepster, B. M., J Org Chem 1978, 43, 4720-4745.
29. Nagarjan, K.; Shelley, K. P.; Perkins, R. R.; Stewart, R., Can J Chem 1987, 65, 1729-1733.
30. Zhuang, R.; Xu, J.; Cai, Z.; Tang, G.; Fang, M.; Zhao, Y., Org Lett 2011, 13, 2110-2113.
31. Bennett, J. A.; Hope, E. G.; Singh, K.; Stuart, A. M., J Fluorine Chem 2009, 130, 615-620.
32. Machnitzki, P.; Nickel, T.; Stelzer, O.; Landgrafe, C., Eur J Inorg Chem 1998, 7, 1029-1034.
33. Moedritzer, K.; Maier, L.; Groenweghe, L. C. D., J Chem Eng Data 1962, 7, 307-310.
34. Krzysztof, O. T.; Boduszek, B., Tetrahedron 2010, 66, 8661-8666.
35. Bravo-Altimarino, K.; Montchamp, J. L., Tetrahedron Lett 2007, 48, 5755-5759.
36. Latham, K.; Coyle, A. M.; Rix, C. J.; Fowless, A.; White, J. M., Polyhedron 2007, 26, 222-236.
37. Freedman, L. D.; Doak, G. O., J Med Chem 1965, 8, 891-892.
38. Freedman, L. D.; Tauber, H.; Doak, G. O.; Magnuson, H., J. J Am Chem Soc 1953, 75, 1379-1381.
39. Grabiak, R. C.; Miles, J. A.; Schwenzer, G. M., Phosphorus Sulfur 1980, 9, 197-202.
40. Avdeef, A.; Box, K. J.; Comer, J. A. E.; Gilges, M.; Hadley, M.; Hibbert, C.; Patterson, W.; Tam, K. Y., J Pharm Biomed Anal 1999, 20, 631-641.
41. Takács-Novák, K.; Box, K. J.; Avdeef, A., Int J Pharm 1997, 151, 235-248.
42. Szakács Z.; Hägele G.; Tyka R., Anal Chim Acta 2004, 522, 247-258.
43. Orgován G.; Noszál B. J, Pharm Biomed Anal 2011, 54, 958-964.
44. Balogh, G. T.; Gyarmati, B.; Nagy, B.; Molnár, L.; Keserű, G. M., QSAR Comb Sci 2009, 28, 1148-1155.
45. a DB, Advanced Chemistry Development, Inc. Toronto, Ontario, Canada. http://www.acdlabs.com/products/percepta/predictors/pka/, 2010.
46. J. Szegezdi, F. Csizmadia, Presented at the 233rd American Chemical Society National Spring Meeting, March 25-29, CINF41, Chicago, IL. https://www.chemaxon.com/conf/Calculating-pKa-values-of-small-and-large- molecules.pdf, 2007.
47. a Prediction for Organic Acids and Bases; Chapman and Hall: New York, 1981; pp. 109-126.
48. Barber, P; Pellechia, P. J.; Ploehn, H. J.; zur Loye, H.-C., ACS Appl Mater Interfaces 2010, 2, 2553-2559.
49. Avdeef, A., J Pharm Sci 1993, 82, 183-190.
50. Purlee, E. L., J Am Chem Soc 1959, 81, 263-269.
51. Glasoe, P. K.; Long, F. A., J Phys Chem 1960, 64, 188-190.
52. Hwang, T. L.; Shaka, A. J., J Magn Reson, Ser A 1995, 112, 275-279.
53. Perrin, C. L.; Fabian, M. A., Anal Chem 1996, 68, 2127-2134.
54. Szakács, Z.; Béni, S.; Varga, Z.; łrfi, L.; Kéri, G.; Noszál, B., J Med Chem 2005, 48, 249-255.