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Volumn 122, Issue 8, 2000, Pages 1824-1825

Organolanthanide-catalyzed intramolecular hydrophosphination/cyclization of phosphinoalkenes and phosphinoalkynes [12]

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; LANTHANIDE; PHOSPHINE DERIVATIVE;

EID: 0034052958     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993633q     Document Type: Letter
Times cited : (200)

References (49)
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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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    • 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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    • 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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    • note
    • Details of the synthetic and catalytic procedures, as well as characterization data, can be found in the Supporting Information.
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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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    • 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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    • 0000502260 scopus 로고    scopus 로고
    • 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.
    • (1996) Inorg. Chem. , vol.35 , pp. 2546-2548
    • Field, L.D.1    Thomas, I.P.2
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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.
    • (1966) J. Chem. Soc., C , pp. 245-247
    • Davies, J.H.1    Downer, J.D.2    Kirby, P.3
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    • note
    • 2-4 this possibility cannot be rigorously excluded at present.
  • 46
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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.
    • (1991) Tetrahedron: Asymmetry , vol.2 , Issue.7 , pp. 569-592
    • Burk, M.J.1    Feaster, J.E.2    Harlow, R.L.3


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