Additions of PH3 to Monosubstituted Alkenes of the Formula H2C=CH(CH2)x(CF2)yCF 3: Convenient, Multigram Syntheses of a Family of Partially Fluorinated Trialkylphosphines with Modulated Electronic Properties and Fluorous Phase Affinities

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6302-6308

  Alvey, Luke J ^a   Rutherford, Drew ^a   Juliette, Jerrick J J ^a   Gladysz, J A ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001528664     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980692y     Document Type: Article

References (74)

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37. 4: (a) Dictionary of Inorganic Compounds; Chapman & Hall: New York, 1992; Vol. 3, p 3386. (b) Toy, A. D. F. In Comprehensive Inorganic Chemistry; Bailar, J. C., Jr., Emeléus, H. J., Nyholm, R., Trotman-Dickenson, A. F., Eds.; Pergamon: Oxford, 1973; Vol. 2, p 414. (c) Encyclopedia of Inorganic Chemistry; King, R. B., Ed.; Wiley & Sons: New York, 1994; Vol. 6, p 3160.
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39. Ravve, A. Principles of Polymer Chemistry; Plenum Press: New York, 1995; p 38.
40. 1 = 2.94 ± 0.07 s. Accordingly, phosphine ratios were determined using a 45° pulse width, a 10 s relaxation delay, and a 1.6 s acquisition time. Data for experiments in Schemes 1-3 follow.
41. HP = 190 Hz).
42. HP = 192 Hz).
43. HP = 193 Hz).
44. HP = 190 Hz).
45. HP = 190 Hz).
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54. Earlier syntheses: (a) Umemoto, T.; Kuriu, Y. Tetrahedron Lett. 1981, 22, 5197. (b) Umemoto, T.; Kuriu, Y.; Nakayama, S.-i. Tetrahedron Lett. 1982, 23, 1169. (c) Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (d) Hu, C.-M.; Qing, F.-L.; Huang, W.-Y. J. Org. Chem. 1991, 56, 2801. (e) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191. (f) Yamamoto, Y.; Saito, K. Organometallics 1997, 16, 2207. (g) Napoli, M.; Gambaretto, G. P. J. Fluorine Chem. 1997, 84, 101.
55. Earlier syntheses: (a) Umemoto, T.; Kuriu, Y. Tetrahedron Lett. 1981, 22, 5197. (b) Umemoto, T.; Kuriu, Y.; Nakayama, S.-i. Tetrahedron Lett. 1982, 23, 1169. (c) Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (d) Hu, C.-M.; Qing, F.-L.; Huang, W.-Y. J. Org. Chem. 1991, 56, 2801. (e) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191. (f) Yamamoto, Y.; Saito, K. Organometallics 1997, 16, 2207. (g) Napoli, M.; Gambaretto, G. P. J. Fluorine Chem. 1997, 84, 101.
56. Earlier syntheses: (a) Umemoto, T.; Kuriu, Y. Tetrahedron Lett. 1981, 22, 5197. (b) Umemoto, T.; Kuriu, Y.; Nakayama, S.-i. Tetrahedron Lett. 1982, 23, 1169. (c) Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (d) Hu, C.-M.; Qing, F.-L.; Huang, W.-Y. J. Org. Chem. 1991, 56, 2801. (e) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191. (f) Yamamoto, Y.; Saito, K. Organometallics 1997, 16, 2207. (g) Napoli, M.; Gambaretto, G. P. J. Fluorine Chem. 1997, 84, 101.
57. Earlier syntheses: (a) Umemoto, T.; Kuriu, Y. Tetrahedron Lett. 1981, 22, 5197. (b) Umemoto, T.; Kuriu, Y.; Nakayama, S.-i. Tetrahedron Lett. 1982, 23, 1169. (c) Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (d) Hu, C.-M.; Qing, F.-L.; Huang, W.-Y. J. Org. Chem. 1991, 56, 2801. (e) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191. (f) Yamamoto, Y.; Saito, K. Organometallics 1997, 16, 2207. (g) Napoli, M.; Gambaretto, G. P. J. Fluorine Chem. 1997, 84, 101.
58. Earlier syntheses: (a) Umemoto, T.; Kuriu, Y. Tetrahedron Lett. 1981, 22, 5197. (b) Umemoto, T.; Kuriu, Y.; Nakayama, S.-i. Tetrahedron Lett. 1982, 23, 1169. (c) Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (d) Hu, C.-M.; Qing, F.-L.; Huang, W.-Y. J. Org. Chem. 1991, 56, 2801. (e) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191. (f) Yamamoto, Y.; Saito, K. Organometallics 1997, 16, 2207. (g) Napoli, M.; Gambaretto, G. P. J. Fluorine Chem. 1997, 84, 101.
59. Earlier syntheses: (a) Umemoto, T.; Kuriu, Y. Tetrahedron Lett. 1981, 22, 5197. (b) Umemoto, T.; Kuriu, Y.; Nakayama, S.-i. Tetrahedron Lett. 1982, 23, 1169. (c) Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (d) Hu, C.-M.; Qing, F.-L.; Huang, W.-Y. J. Org. Chem. 1991, 56, 2801. (e) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191. (f) Yamamoto, Y.; Saito, K. Organometallics 1997, 16, 2207. (g) Napoli, M.; Gambaretto, G. P. J. Fluorine Chem. 1997, 84, 101.
60. Earlier syntheses: (a) Umemoto, T.; Kuriu, Y. Tetrahedron Lett. 1981, 22, 5197. (b) Umemoto, T.; Kuriu, Y.; Nakayama, S.-i. Tetrahedron Lett. 1982, 23, 1169. (c) Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (d) Hu, C.-M.; Qing, F.-L.; Huang, W.-Y. J. Org. Chem. 1991, 56, 2801. (e) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191. (f) Yamamoto, Y.; Saito, K. Organometallics 1997, 16, 2207. (g) Napoli, M.; Gambaretto, G. P. J. Fluorine Chem. 1997, 84, 101.
61. This compound has been described in patents in the following Chemical Abstracts citations: (a) Hansen, R. L. 1967, 67, 63788. (b) Masahiro, I. 1994, 121, 280253. (c) Masahiro, I. 1995, 122, 105246.
62. This compound has been described in patents in the following Chemical Abstracts citations: (a) Hansen, R. L. 1967, 67, 63788. (b) Masahiro, I. 1994, 121, 280253. (c) Masahiro, I. 1995, 122, 105246.
63. This compound has been described in patents in the following Chemical Abstracts citations: (a) Hansen, R. L. 1967, 67, 63788. (b) Masahiro, I. 1994, 121, 280253. (c) Masahiro, I. 1995, 122, 105246.
64. This compound has been described once previously in a patent. Chemical Abstracts citation: Meinert, H. 1997, 126, 250892.
65. (a) Bhattacharya, A. K.; Roy, N. K. The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley & Sons: New York, 1992; Vol. 2, p 197.
66. (b) Gilheany, D. G.; Mitchell, C. M. The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley & Sons: New York 1990; Vol. 1, p 167.
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72. 3 was calculated as follows. The alkene volume (6.90 g ÷ 1.52 g/mL = 4.54 mL in the preparation of 1) and the stirring bar volume (0.4 mL) were subtracted from the autoclave volume (30 mL). and the difference utilized in the inert gas equation, n = PV/RT (T = 298 K; 75 psi gauge reading = 5.1 atm above ambient pressure, or 6.1 atm total).
73. For the graphical method used to obtain the melting point, see Cammenga, H. K.; Epple, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1171; Angew. Chem. 1995, 107, 1284.
74. For the graphical method used to obtain the melting point, see Cammenga, H. K.; Epple, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1171; Angew. Chem. 1995, 107, 1284.