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Volumn 131, Issue 8, 2009, Pages 3078-3092

Anatomy of phobanes. Diastereoselective synthesis of the three isomers of n-butylphobane and a comparison of their donor properties

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; HELIUM; PLATINUM; RHODIUM COMPOUNDS;

EID: 84908659785     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808807s     Document Type: Article
Times cited : (34)

References (75)
  • 1
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    • (a) Mulders, J. P. Neth. Patent 1966, 6, 604 09 to Shell.
    • (1966) Neth. Patent , vol.6 , pp. 604-609
    • Mulders, J.P.1
  • 2
    • 84908704436 scopus 로고
    • U.S. Patent, 3, 400 163 to Shell
    • (b) Winkle, J. L. V.; Mason, R. F. U.S. Patent 1968, 3, 400 163 to Shell.
    • (1968)
    • Winkle, J.L.V.1    Mason, R.F.2
  • 6
    • 84908704575 scopus 로고
    • to Hoechst. Mixtures of s-PhobPH and a-PhobPH are now commercially available as solutions in toluene. The proportions of the isomers depend on the supplier
    • Elsner, G.; Heymer, G.; Stephan, H.-W. German Patent 1978, 2, 703 802 to Hoechst. Mixtures of s-PhobPH and a-PhobPH are now commercially available as solutions in toluene. The proportions of the isomers depend on the supplier.
    • (1978) German Patent , vol.2 , pp. 703-802
    • Elsner, G.1    Heymer, G.2    Stephan, H.-W.3
  • 8
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    • Robertson, A. J. World Patent 2000, WO 00/52017 to Cytec.
    • Robertson, A. J. World Patent 2000, WO 00/52017 to Cytec.
  • 9
    • 2742535506 scopus 로고    scopus 로고
    • 7-PhobPBu, 9-anti-butyl-9-phosphabicyclo[4.2.1]nonane.
    • 7-PhobPBu, 9-anti-butyl-9-phosphabicyclo[4.2.1]nonane.
  • 24
    • 84908704568 scopus 로고    scopus 로고
    • Drent, E.; Van Broekhoven, J. A. M.; Breed, A. J. M. World Patent 2003, WO 03040065 to Shell.
    • Drent, E.; Van Broekhoven, J. A. M.; Breed, A. J. M. World Patent 2003, WO 03040065 to Shell.
  • 43
    • 84908704433 scopus 로고    scopus 로고
    • a is logarithmic, the conclusion of a difference of ∼2 units between a-PhobPH and s-PhobPH should be robust.
    • a is logarithmic, the conclusion of a difference of ∼2 units between a-PhobPH and s-PhobPH should be robust.
  • 44
    • 84908704325 scopus 로고    scopus 로고
    • Arnoldy, P.; Bolinger, C. M.; Drent, E. Eberhard, M. R.; Heeres, H. J.; Van Der Linden, A. J.; Mul, P. M.; Pringle, P. G.; Suykerbuyk, J. C. L. J.; Tau, K. D. World Patent 2002, WO 02064250, to Shell.
    • Arnoldy, P.; Bolinger, C. M.; Drent, E. Eberhard, M. R.; Heeres, H. J.; Van Der Linden, A. J.; Mul, P. M.; Pringle, P. G.; Suykerbuyk, J. C. L. J.; Tau, K. D. World Patent 2002, WO 02064250, to Shell.
  • 45
    • 84908704213 scopus 로고    scopus 로고
    • The assignment of the minor species as a7-PhobPH was validated by the addition of genuine s-PhobPH to a sample of the mixture of a 5PhobPH and a7-PhobPH and three distinct 31P NMR signals were observed at-48.4,-54.1, and-54.3 ppm. Furthermore, addition of BH3 · THF to the 3:1:1 mixture of a5-PhobPH, a 7-PhobPH, and s-PhobPH gave a 3:1:1 mixture of a 5-PhObPH(BH3, a7-PhObPH(BH3, and s-PhObPHBH3
    • 3).
  • 49
    • 36849064333 scopus 로고    scopus 로고
    • The lack of stereoselectivity in the a-PhobPCl substitution reaction may be due to frontside and backside nucleophilic attack, see for example van Bochove, M. A, Swart, M, Bickelhaupt, F. M. ChemPhysChem 2007, 8, 2452
    • The lack of stereoselectivity in the a-PhobPCl substitution reaction may be due to frontside and backside nucleophilic attack, see for example van Bochove, M. A.; Swart, M.; Bickelhaupt, F. M. ChemPhysChem 2007, 8, 2452.
  • 53
    • 84908704565 scopus 로고    scopus 로고
    • 3 but are in the same descending order.
    • 3 but are in the same descending order.
  • 57
    • 84908704564 scopus 로고    scopus 로고
    • -1 (298 K).
    • -1 (298 K).
  • 61
    • 36448983228 scopus 로고    scopus 로고
    • Phosphacycles have recently attracted considerable attention in hydroformylation catalysis. For leading references see: a
    • Phosphacycles have recently attracted considerable attention in hydroformylation catalysis. For leading references see: (a) Müller, C.; Vogt, D. Dalton Trans. 2007, 5505.
    • (2007) Dalton Trans , pp. 5505
    • Müller, C.1    Vogt, D.2
  • 67
    • 84908704323 scopus 로고    scopus 로고
    • 2) which was present in the commercial phobane. This caused no problems with the purity of the derivatives.
    • 2) which was present in the commercial phobane. This caused no problems with the purity of the derivatives.
  • 68
    • 84908704431 scopus 로고    scopus 로고
    • SHELXTL program system version 5.1; Bruker Analytical X-ray Instruments Inc, Madison, WI, 1998
    • SHELXTL program system version 5.1; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
  • 69
    • 84908704211 scopus 로고    scopus 로고
    • Jaguar, version 6.0; Schrödinger, LLC: New York, 2005
    • Jaguar, version 6.0; Schrödinger, LLC: New York, 2005.
  • 75
    • 84908704563 scopus 로고    scopus 로고
    • Test calculations using the more stringent default convergence criteria did not lead to significant changes in energies, bond lengths, or angles but were much more time-consuming
    • Test calculations using the more stringent default convergence criteria did not lead to significant changes in energies, bond lengths, or angles but were much more time-consuming.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.