Reaction of perfluoroalkyl Grignard reagents with phosphorus trihalides: A new route to perfluoroalkyl-phosphonous and-phosphonic acids

Inorganic Chemistry

Volumn 50, Issue 4, 2011, Pages 1484-1490

  Hosein, Adil I ^a   Le Goff, Xavier F ^b   Ricard, Louis ^b   Caffyn, Andrew J M ^a,c  

^a UNIVERSITY OF THE WEST INDIES   (Trinidad and Tobago)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

^c MANCHESTER METROPOLITAN UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951636754     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic102063e     Document Type: Article

References (82)

1. Heid, C., Hoffmann, D., and Polster, J. Ger. Offen. 2,233,941, 1974.
2. Haky, J. E., Blauvelt, T. M., and Wieserman, L. F. J. Liquid Chromatogr. Relat. Technol. 1996, 19, 307-332
3. Mori, M. and Sakurai, O. Jpn. Kokai Tokkyo Koho 6199061, 1994.
4. Mohajer, Yanackal, A., Sharma, J., Hsiao, Y.-L., Mininni, R., Thomas, B., and Zhu, J. PCT Int. Appl. 018592, 2003.
5. Araki, T., Tanaka, Y., Andou, Y., and Komatsu, Y. PCT Int. Appl. 091343, 2003.
6. Saito, Y. and Horiuchi, Y. PCT Int. Appl. 081658, 2003.
7. Bhamidipati, M., Lazaro, E., Lyons, F., and Morris, R. S. Mater. Res. Soc. Symp. Proc. 1998, 496, 217-222
8. Yoshitake, M., Kunisa, Y., and Yoshida, N. Jpn. Kokai Tokkyo Koho 11339824, 1999.
9. Yoshitake, M., Yoshida, N., Kunisa, Y., and Shimodaira, S. Jpn. Kokai Tokkyo Koho 11135135, 1999.
10. Yoshitake, M., Endo, E., and Kunisa, Y. Jpn. Kokai Tokkyo Koho 11307108, 1999.
11. Yoshitake, M., Yoshida, N., Kokusa, Y., and Shimodaira, S. Jpn. Kokai Tokkyo Koho 11135136, 1999.
12. Kimoto, K. PCT Int. Appl. 063991, 2000.
13. Li, S., Zhou, Z., Liu, M., and Li, W. PCT Int. Appl. 072413, 2005.
14. Motomura, A., Tayanagi, J., Saito, M., and Endo, E. Jpn. Kokai Tokkyo Koho 012520, 2007.
15. Bhushan, B., Cichomski, M., Hoque, E., DeRose, J. A., Hoffmann, P., and Mathieu, H. J. Microsyst. Technol. 2006, 12, 588-596
16. Bennett, F. W., Brandt, G. R. A., Emeléus, H. J., and Haszeldine, R. N. Nature 1950, 166, 225
17. Bennett, F. W., Emeléus, H. J., and Haszeldine, R. N. J. Chem. Soc. 1953, 1565-1571
18. Bennett, F. W., Emeléus, H. J., and Haszeldine, R. N. J. Chem. Soc. 1954, 3598-3603
19. Bennett, F. W., Emeléus, H. J., and Haszeldine, R. N. J. Chem. Soc. 1954, 3896-3904
20. Emeléus, H. J. and Smith, J. D.. J. Chem. Soc. 1959, 375-381
21. Brecht, H. Ger. Offen. 2,110,769, 1972.
22. Brecht, H. and Hoffmann, D. Ger. Offen. 2,110,767, 1972.
23. Mahmood, T. and Shreeve, J. M. Inorg. Chem. 1986, 25, 3128-3131
24. Maslennikov, I. G., Laurent?ev, A. N., Khovanskaya, N. V., Lebedev, V. B., and Sochilin, E. G. J. Gen. Chem. USSR 1979, 49, 1307-1309
25. Yagupol'skii, L. M., Semenii, V. Ya., Zavatskii, V. N., Bil?dinov, K. N., and Kirsanov, A. V. J. Gen. Chem. USSR 1984, 54, 692-695
26. Kovaleva, T. V., Martynyukh, E. G., and Semenii, V. Ya. J. Gen. Chem. USSR 1989, 59, 2245-2248
27. Ignat?ev, N. and Sartori, P. J. Fluorine Chem. 2000, 103, 57-61
28. Kampa, J. J., Nail, J. W., and Lagow, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1241-1244
29. Murphy-Jolly, M. B., Lewis, L. C., and Caffyn, A. J. M. Chem. Commun. 2005, 4479-4480
30. Hoge, B. and Thösen, C. Inorg. Chem. 2001, 40, 3113-3116
31. Vaillard, S. Eostigo, A., and Rossi, R. A. Organometallics 2004, 23, 3003-3007
32. Eisenberger, P., Kieltsch, I., Armanino, N., and Togni, A. Chem. Commun. 2008, 1575-1577
33. Brisdon, A. K. and Herbert, C. J. Chem. Commun. 2009, 6658-6660
34. Lewis-Alleyne, L. C., Murphy-Jolly, M. B., Le Goff, X. F., and Caffyn, A. J. M. Dalton Trans. 2010, 39, 1198-1200
35. Lanteri, M. N., Rossi, R. A., and Martin, S. E. J. Organomet. Chem. 2009, 694, 3425-3430
36. Phelps, J. E., Frawley, S. B., and Peters, R. G. Heteroat. Chem. 2009, 20, 393-397
37. Burton, D. J. and Yang, Z.-Y. Tetrahedron 1992, 48, 189-275
38. Haszeldine, R. N. Nature 1951, 167, 139-140
39. Kvíçala, Ştambaský, J. J., Skalický, M., and Paleta, O. J. Fluorine Chem. 2005, 126, 1390-1395
40. Peters, R. G., Bennett, B. L., Schnabel, R. C., and Roddick, D. M. Inorg. Chem. 1997, 36, 5962-5965
41. Roddick, D. M. Chem. Eng. News 1997, 75 (40) 6
42. Krause, L. J. and Morrison, J. A. J. Am. Chem. Soc. 1981, 103, 2995-3001
43. Ganja, E. A., Ontiveros, C. D., and Morrison, J. A. Inorg. Chem. 1988, 27, 4535-4538
44. Ganja, E. A. and Morrison, J. A. Inorg. Chem. 1990, 29, 33-38
45. Auger, V. and Billy, B. C. R. 1904, 139, 597-599
46. Hibbert, H. Ber. 1906, 39, 160-162
47. Kharasch, M. S. and Reinmuth, O. Grignard Reactions of Nonmetallic Substances; Constable & Co. Ltd.: London, U.K., 1954.
48. Silverman, G. S. Nucleophilic Substitution with Electrophilic Organic, Main Group and Transition Metal Species. In Handbook of Grignard Reagents; Silverman, G. S. and Rakita, P. E., Eds.; Marcel Dekker Inc.: New York, 1996; pp 307- 354.
49. Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley-Interscience: New York, 2000.
50. McBee, E. T., Roberts, C. W., and Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335-337
51. Denson, D. D., Smith, C. F., and Tamborski, C. J. Fluorine Chem. 1973/74, 3, 247-258
52. Burg, A. B. and Griffiths, J. E. J. Am. Chem. Soc. 1961, 83, 4333-4337
53. Harris, G. S. J. Chem. Soc. 1958, 512-519
54. Haszeldine, R. N. J. Chem. Soc. 1952, 3423-3428
55. Howells, R. D. and Gilman, H. J. Fluorine Chem. 1975, 5, 99-114
56. Thoai, N. J. Fluorine Chem. 1975, 5, 115-125
57. Smith, C. F., Soloski, E. J., and Tamborski, C. J. Fluorine Chem. 1974, 4, 35-45
58. Chambers, R. D., Musgrave, W. K. R., and Savory, J. J. Chem. Soc. 1962, 1993-1999
59. Haszeldine, R. N. J. Chem. Soc. 1954, 1273-1279
60. McBee, E. T., Battershell, R. D., and Braendlin, H. P. J. Org. Chem. 1963, 28, 1131-1133
61. Gilman, H. and Vernon, C. C. J. Am. Chem. Soc. 1926, 48, 1063-1066
62. Cao, G., Hong, H.-G., and Mallouk, T. E. Acc. Chem. Res. 1992, 25, 420-427
63. Bauer, E. M., Bellitto, C., Colapietro, M., Ibrahim, S. A., Mahmoud, M. Rortalone, G., and Righini, G. J. Solid State Chem. 2006, 179, 389-397
64. Bujoli, Bena, Oalvadeau, P., Le Bideau, Jayen, C., and Rouxel, J. Chem. Mater. 1993, 5, 583-587
65. Bellitto, C., Bauer, E. M., Leone, P., Meerschaut, A., Guillot-Deudon, C., and Righini, G. J. Solid State Chem. 2006, 179, 579-589
66. Le Bideau, J., Bujoli, B., Jouanneaux, Aayen, Calvadeau, P., and Rouxel, J. Inorg. Chem. 1993, 32, 4617-4620
67. Adair, B. A., Neeraj, S., and Cheetham, A. K. Chem. Mater. 2003, 15, 1518-1529
68. Khan, M. I., Lee, Y.-S., O?Connor, C. J., Haushalter, R. C., and Zubieta, J. Chem. Mater. 1994, 6, 721-723
69. Harrison, W. T. A., Dussack, L. L., and Jacobsen, A. J. Acta Crystallogr., Sect C 1997, 53, 200-202
70. Langley, S., Helliwell, M., Sessoli, R., Teat, S. J., and Winpenny, R. E. P. Inorg. Chem. 2008, 47, 497-507
71. Cao, G., Lynch, V. M., Swinnea, J. S., and Mallouk, T. E. Inorg. Chem. 1990, 29, 2112-2117
72. Yuge, T., Kai, N., Hisaki, I., Miyata, M., and Norimitsu, T. Chem. Lett. 2007, 36, 1390-1391
73. Driss, H., Boubekeur, K., Debbabi, M., and Thouvenot, R. Eur. J. Inorg. Chem. 2008, 3678-3686
74. Singh, R. P., Twamley, B., and Shreeve, J. M. J. Chem. Soc., Dalton Trans. 2000, 4089-4092
75. Pantenburg, I., Thösen, C., and Hoge, B. Z. Anorg. Allg. Chem. 2002, 628, 1785-1788
76. Engel, R. and Cohen, J. I. Synthesis of Carbon-Phosphorus Bonds, 2 nd ed.; CRC Press: Boca Raton, FL, 2004.
77. Voskuil, W. and Arens, J. F. Recl. Trav. Chim. Pays-Bas 1963, 82, 302-304
78. Wall, L. A., Donadio, R. E., and Pummer, W. J. J. Am. Chem. Soc. 1960, 82, 4846-4848
79. Magnelli, D., Tesi, G., Lowe, J., Jr., and McQuistion, W. Inorg. Chem. 1966, 5, 457-461
80. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. Golidori, G., and Spagna, R. SIR97, An integrated package of computer programs for the solution and refinement of crystal structures using single crystal data; J. Appl. Crystallogr. 1999, 32, 115- 119.
81. Sheldrick, G. M. SHELXL-97; Universität Göttingen: Göttingen, Germany, 1997.
82. Farrugia, L. J. Ortep-3 for Windows; J. Appl. Crystallogr. 1997, 30, 565.