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(a) For a review of early work in acylphosphine chemistry, including examples of phthaloylphosphine preparations, see: Becker, G.; Mundt, O. Phosphorus Sulfur Relat. Elem. 1983, 14, 267-83.
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Becker, G.1
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37049066598
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(b) A single P-coordinated iron(0) tetracarbonyl complex of phenylphthaloylphosphine has been reported, along with examples of P-C cleavage and oxidation at the phosphorus atom: Barron, A. R.; Hall, S. W.; Cowley, A. H. J. Chem. Soc., Chem. Commun. 1987, 1753-1754.
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Barron, A.R.1
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84963463662
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(c) Nickel(0) and iron(0) carbonyl complexes of 1-adamantyldipivaloylphosphine have been prepared: Goerlich, J. R.; Mueller, C.; Schmutzler, R. Phosphorus Sulfur Silicon Relat. Elem. 1993, 85, 193-205.
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Goerlich, J.R.1
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O'Brien, B.A.1
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Ph.D. Thesis, Georgia Institute of Technology
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McLaughlin, M. L. Ph.D. Thesis, Georgia Institute of Technology, 1983.
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McLaughlin, M.L.1
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(a) Becker, G.; Rössler, M.; Uhl, G. Z. Anorg. Allg. Chem. 1982, 495, 73-88.
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Becker, G.1
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(b) Becker, G.; Beck, H. P. Angew. Chem., Int. Ed. Engl. 1980, 19, 741-742;
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Angew. Chem. 1980, 92, 756-757.
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0011484799
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- and will be used in the present discussion.
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17
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84980158818
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(a) Schmidpeter, A.; Zwaschka, F. Angew. Chem., Int. Ed. Engl. 1977, 16, 704-705;
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Schmidpeter, A.1
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Schmidpeter, A.1
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Angew. Chem. 1979, 91, 441-442.
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21
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Sheldrick, W.S.1
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0010954530
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Angew. Chem. 1979, 91, 998-999.
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Cotton, F.A.1
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0002083470
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(a) Howell, J. A. S.; Lovatt, J. D.; Mcardle, P.; Cunningham, D.; Maimone, E.; Gottlieb, H. E.; Goldschmidt, Z. Inorg. Chem. Commun. 1998, 1, 118-120.
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33749087284
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(b) Howell, J. A. S.; Fey, N.; Lovatt, J. D.; Yates, P. C.; McArdle, P.; Cunningham, D.; Sadeh, E.; Gottlieb, H. E.; Goldschmidt, Z.; Hursthouse, M. B.; Light, M. E. J. Chem. Soc., Dalton Trans. 1999, 17, 3015-3028.
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Cunningham, D.6
Sadeh, E.7
Gottlieb, H.E.8
Goldschmidt, Z.9
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Albers, M. O.; Singleton, E.; Coville, N. J. Inorg. Synth. 1989, 26, 62.
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Albers, M.O.1
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30
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0003887404
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note; Harper and Row: New York
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For example, the well-known Hammett constants, used in the study of ring substituent effects, are derived from ionization equilibria of substituted benzoic acids. For a thorough discussion, see: Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper and Row: New York, 1987; pp 143-159.
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Lowry, T.H.1
Richardson, K.S.2
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0002180264
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Liotta, C. L.; McLaughlin, M. L.; VanDerveer, D. G.; O'Brien, B. A. Tetrahedron Lett. 1984, 1665-1668.
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Liotta, C.L.1
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O'Brien, B.A.4
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37
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85050953884
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note
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A synthetic equivalent of dihydrogenphosphide has been generated in situ in DMSO by reaction with KOH; in that case it is assumed that the deprotonation is facilitated through absorption, by excess KOH, of the water that is produced in the reaction: Jolly, W. L. Inorg. Synth. 1968, 11, 124-126.
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Inorg. Synth.
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Jolly, W.L.1
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38
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0011392713
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note
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2 should prove to be of use in other areas of phosphorus chemistry. A reviewer suggested that, for preparation of potassium phthaloylphosphides, commercially available potassium tert-butoxide solution be used in preference to generation of the potassium tert-alkoxide by reaction of potassium metal with the alcohol.
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39
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0004152586
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note; Pergamon Press: Oxford, U.K.
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It is assumed that the actual phosphine pressure does not reach the upper limit calculated from the free volume of the reaction vessel, since phosphine has significant solubility in organic solvents: Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Pergamon Press: Oxford, U.K., 1997; p 493.
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Chemistry of the Elements
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Greenwood, N.N.1
Earnshaw, A.2
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40
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0011393937
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note
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31P NMR indicates to be a complex mixture of products.
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