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Hydrophosphination mediated by Pd, Pt, Ni complexes: (a) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039-5040. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571-1572. (c) Hoye, P. A.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-74. (d) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702.
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Bond enthalpy data: (a) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. ACS Symp. Ser. 1990, 428, 159-174. (b) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853.
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0342304062
-
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note
-
AM-1 level calculations indicate that addition of methyl phosphine to ethylene is exothermic by ∼-15 kcal/mol, while addition to acetylene is exothermic by ∼-38 kcal/mol. We thank Dr. Albert Israel for these calculations.
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18
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(a) Laurenco, C.; Villien, L.; Kaufmann, G. Tetrahedron 1984, 40, 2731-2740.
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(a) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376.
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(b) Burk, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423-4424.
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0002620936
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Marthinho Simoes, J. A., Ed.; Kluwer: Dordrecht
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50reliminary observations: Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Marthinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
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Syntheses of primary and secondary phosphines: (a) Guillemin, J. C.; Savignac, P.; Denis, J. M. Inorg. Chem. 1991, 30, 2170-2173. (b) Cabioch, I. L.; Denis, J. M. J. Organomet. Chem. 1989, 377, 227-233. (c) Wolfsberger, W. Chem. Zeitung 1988, 112, 379-381. (d) Kosolapoff, G. M.; Maeir, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972; Vol. 1, pp 1-287.
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Syntheses of primary and secondary phosphines: (a) Guillemin, J. C.; Savignac, P.; Denis, J. M. Inorg. Chem. 1991, 30, 2170-2173. (b) Cabioch, I. L.; Denis, J. M. J. Organomet. Chem. 1989, 377, 227-233. (c) Wolfsberger, W. Chem. Zeitung 1988, 112, 379-381. (d) Kosolapoff, G. M.; Maeir, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972; Vol. 1, pp 1-287.
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0001496937
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Syntheses of primary and secondary phosphines: (a) Guillemin, J. C.; Savignac, P.; Denis, J. M. Inorg. Chem. 1991, 30, 2170-2173. (b) Cabioch, I. L.; Denis, J. M. J. Organomet. Chem. 1989, 377, 227-233. (c) Wolfsberger, W. Chem. Zeitung 1988, 112, 379-381. (d) Kosolapoff, G. M.; Maeir, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972; Vol. 1, pp 1-287.
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Wolfsberger, W.1
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0001496937
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Wiley-Interscience: New York
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Syntheses of primary and secondary phosphines: (a) Guillemin, J. C.; Savignac, P.; Denis, J. M. Inorg. Chem. 1991, 30, 2170-2173. (b) Cabioch, I. L.; Denis, J. M. J. Organomet. Chem. 1989, 377, 227-233. (c) Wolfsberger, W. Chem. Zeitung 1988, 112, 379-381. (d) Kosolapoff, G. M.; Maeir, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972; Vol. 1, pp 1-287.
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Organic Phosphorus Compounds
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Kosolapoff, G.M.1
Maeir, L.2
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0343173619
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3: ref 11c
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3: ref 11c.
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33
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0342739153
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(b) Li/THF: Chou, T.-S.; Yuan, J.-J.; Tsao, C.-H. J. Chem, Res. (S), 1985, 18-19.
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(c) Li and Na cleavage methods: Budzelaar, P. H. M.; Doom, J. A.; Meijboom, N. Recl. Trav. Chim. Pays-Bas 1991, 110, 420-432.
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35
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0343173617
-
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note
-
Details of the synthetic and catalytic procedures, as well as characterization data, can be found in the Supporting Information.
-
-
-
-
39
-
-
0000488844
-
-
Examples of P-H addition to olefins to form phospolanes and phosphorinanes: (a) Hackney, M. L.; Schubert, D. M.; Brandt, P. F.; Haltiwanger, R. C.; Norman, A. D. Inorg. Chem. 1997, 36, 1867-1872. (b) Brandt, P. F.; Schubert, D. M.; Norman, A. D. Inorg. Chem. 1997, 36, 1728- 1731. (c) Field, L. D.; Thomas, I. P. Inorg. Chem. 1996, 35, 2546-2548. (d) Davies, J. H.; Downer, J. D.; Kirby, P. J. Chem. Soc., C 1966, 245-247.
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Hackney, M.L.1
Schubert, D.M.2
Brandt, P.F.3
Haltiwanger, R.C.4
Norman, A.D.5
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40
-
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0000488844
-
-
Examples of P-H addition to olefins to form phospolanes and phosphorinanes: (a) Hackney, M. L.; Schubert, D. M.; Brandt, P. F.; Haltiwanger, R. C.; Norman, A. D. Inorg. Chem. 1997, 36, 1867-1872. (b) Brandt, P. F.; Schubert, D. M.; Norman, A. D. Inorg. Chem. 1997, 36, 1728-1731. (c) Field, L. D.; Thomas, I. P. Inorg. Chem. 1996, 35, 2546-2548. (d) Davies, J. H.; Downer, J. D.; Kirby, P. J. Chem. Soc., C 1966, 245-247.
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Brandt, P.F.1
Schubert, D.M.2
Norman, A.D.3
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41
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0000502260
-
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Examples of P-H addition to olefins to form phospolanes and phosphorinanes: (a) Hackney, M. L.; Schubert, D. M.; Brandt, P. F.; Haltiwanger, R. C.; Norman, A. D. Inorg. Chem. 1997, 36, 1867-1872. (b) Brandt, P. F.; Schubert, D. M.; Norman, A. D. Inorg. Chem. 1997, 36, 1728- 1731. (c) Field, L. D.; Thomas, I. P. Inorg. Chem. 1996, 35, 2546-2548. (d) Davies, J. H.; Downer, J. D.; Kirby, P. J. Chem. Soc., C 1966, 245-247.
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Field, L.D.1
Thomas, I.P.2
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42
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37049136347
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Examples of P-H addition to olefins to form phospolanes and phosphorinanes: (a) Hackney, M. L.; Schubert, D. M.; Brandt, P. F.; Haltiwanger, R. C.; Norman, A. D. Inorg. Chem. 1997, 36, 1867-1872. (b) Brandt, P. F.; Schubert, D. M.; Norman, A. D. Inorg. Chem. 1997, 36, 1728- 1731. (c) Field, L. D.; Thomas, I. P. Inorg. Chem. 1996, 35, 2546-2548. (d) Davies, J. H.; Downer, J. D.; Kirby, P. J. Chem. Soc., C 1966, 245-247.
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Davies, J.H.1
Downer, J.D.2
Kirby, P.3
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43
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0343173614
-
-
note
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2-4 this possibility cannot be rigorously excluded at present.
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45
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84981881918
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(b) Rauk, A.; Allen, L. C.; Mislow, K. Angew. Chem., Int. Ed. Engl. 1970, 9, 400-414.
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Rauk, A.1
Allen, L.C.2
Mislow, K.3
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46
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0025886768
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The δ 10.4 ppm signal corresponds to the (R,R) or (S,S) isomer, prepared by an alternative route: Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2(7), 569-592.
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Burk, M.J.1
Feaster, J.E.2
Harlow, R.L.3
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47
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33845376846
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Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103.
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Tian, S.; Arredondo, V. A.; Stern, C. L.; Marks, T. J. Organometallics 1999, 18, 2568-2570.
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