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(b) Steltzer, O.; Langhans, K.P. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: New York, 1990; Vol. 1, Chapter 8.
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When the chain length between the dihalide is less than three carbons long, the reaction can lead to the formation of phosphirans, see: a, Barton, D, Ollis, W.D, Eds, Pergamon Press: UK
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When the chain length between the dihalide is less than three carbons long, the reaction can lead to the formation of phosphirans, see: (a) Smith, D.J.H. In Comprehensive Organic Synthesis; Barton, D.; Ollis, W.D., Eds.; Pergamon Press: UK, 1979, Vol. 2, pp. 1138-1139.
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Smith, D.J.H.1
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21
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84981835462
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For generation of phosphide anions, see: b
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For generation of phosphide anions, see: (b) Issleib, K.; Weichmann, H. Chem. Ber. 1968, 101, 2197.
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Issleib, K.1
Weichmann, H.2
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24
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0004195923
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Hartley, F.R, Ed, Wiley: New York, Chapter 8
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Steltzer, O.; Langhans, K.P. In The Chemistry of Organophosphorus Compounds; Hartley, F.R., Ed.; Wiley: New York, 1990; Vol. 1, Chapter 8.
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0141894181
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Honaker, M.T.; Sandefur, B.J.; Hargett, J.L. McDaniel, A.L. Salvatore, R.N. Tetrahedron Lett. 2003, 44, 8373.
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Sandefur, B.J.2
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Salvatore, R.N.5
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Phosphorus, Sulfur, and Silicon, and Relat. Elem
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Honaker, M.T.; Salvatore, R.N. Phosphorus, Sulfur, and Silicon, and Relat. Elem. 2004, 2, 277.
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Salvatore, R.N.2
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46149094539
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Molecular sieves accelerated the alkylation by removal of water from the reaction media, at °C prior to use, reactions were sluggish resulting in diminished product yields with recovery of the starting phosphine predominately
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Molecular sieves accelerated the alkylation by removal of water from the reaction media. When molecular sieves were not activated by drying for 24 b at 120 °C prior to use, reactions were sluggish resulting in diminished product yields with recovery of the starting phosphine predominately.
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When molecular sieves were not activated by drying for 24 b
, pp. 120
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28
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46149097536
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General Procedure for the Synthesis of Disecondary Phosphines, 3a-f, Representative procedure for 1,2-bis(phenylphosphino) ethane, 3b, To a suspension containing activated powdered 4 Å molecular sieves (2 g) in anhydrous N,N-dimethylformamide (18.2 mL) cesium hydroxide monohydrate (1.22 g, 7.28 mmol) was added and the mixture was stirred under a dry nitrogen atmosphere. After phenylphosphine (0.4 mL, 3.36 mmol, 1) was added, the reaction mixture was stirred for 1 hour resulting in a deep colored yellow solution. 1,2-Dibromoethane (0.16 mL, 1.82 mmol, 2b) was added in one portion, at which point, the mixture turned immediately to milky white. The reaction was allowed to proceed at room temperature for 45 h, at which point, 1 was consumed (TLC, Degassed water (30 mL) was added and the mixture was subsequently extracted with CH2Cl2 3 × 30 mL, The combined organic layers were then washed with degassed wate
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2: C, 68.29; H, 6.55; P, 25.16. Found: C, 68.32; H, 6.50.
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29
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3242663729
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Recently, a general method for the sequestering of CuCl and the reclaiming of mono- and bidentate phosphines was reported, see
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Recently, a general method for the sequestering of CuCl and the reclaiming of mono- and bidentate phosphines was reported, see: Lipshutz, B.H.; Frieman, B.; Birkedal, H. Org. Lett. 2004, 6, 2305.
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Org. Lett
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Lipshutz, B.H.1
Frieman, B.2
Birkedal, H.3
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