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Volumn 26, Issue 14, 2007, Pages 3385-3402

Experimental and computational study of the transformation of terminal alkynes to vinylidene ligands on trans-(chloro)bis(phosphine)Rh fragments and effects of phosphine substituents

Author keywords

[No Author keywords available]

Indexed keywords

EYRING MODELS; ISOTOPOMERS; PHOSPHINE SUBSTITUENTS;

EID: 34547304103     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700355r     Document Type: Article
Times cited : (59)

References (117)
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    • Activation and Functionalization of C-H Bonds; Goldberg, K. I., Goldman, A. S., Eds.; American Chemical Society: Washington, D.C., 2004; Vol. 885.
    • (2004) Activation and Functionalization of C-H Bonds , vol.885
  • 8
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    • Dyker, G, Ed, Wiley-VCH: Weinheim, Germany
    • Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Handbook of C-H Transformations
  • 13
    • 0037870702 scopus 로고    scopus 로고
    • In particular, for recent uses of Rh vinylidenes in synthesis: (a) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2003, 125, 7482-7483.
    • In particular, for recent uses of Rh vinylidenes in synthesis: (a) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2003, 125, 7482-7483.
  • 25
  • 31
    • 0001406599 scopus 로고    scopus 로고
    • Reviews on alkane complexes
    • Reviews on alkane complexes: Hall, C.; Perutz, R. N. Chem. Rev. 1996, 96, 3125-3146.
    • (1996) Chem. Rev , vol.96 , pp. 3125-3146
    • Hall, C.1    Perutz, R.N.2
  • 33
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    • Recent leading references: Castro-Rodriguez, I.; Nakai, H.; Gantzel, P.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 15734-15735.
    • Recent leading references: Castro-Rodriguez, I.; Nakai, H.; Gantzel, P.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 15734-15735.
  • 51
    • 17644415706 scopus 로고    scopus 로고
    • While this work was in progress, a computational study of alkyne-to-vinylidene transformation on the simple fragment mms-(chloro) Rh(PH3)2 appeared: Suresh, C. H, Koga, N. J. Theor. Comput. Chem. 2005, 4, 59-73. No other phosphines were considered in this study
    • 2 appeared: Suresh, C. H.; Koga, N. J. Theor. Comput. Chem. 2005, 4, 59-73. No other phosphines were considered in this study.
  • 53
    • 34547314164 scopus 로고    scopus 로고
    • See Supporting Information for full details
    • See Supporting Information for full details.
  • 58
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    • Reference 47
    • (e) Reference 47.
  • 78
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    • The values given in this paper differ slightly from those appearing in our original communication,42 because an empirical fitting of the data has now been supplanted by a rigorous analysis. See Experimental Section and Supporting Information for full details
    • 42 because an empirical fitting of the data has now been supplanted by a rigorous analysis. See Experimental Section and Supporting Information for full details.
  • 83
    • 20944451851 scopus 로고    scopus 로고
    • C-C in acetylene derivatives, see refs 71a-f. (a) Sebald, A.; Wrackmeyer, B. Spectrochim. Acta, Part A 1981, 37A, 365-368.
    • C-C in acetylene derivatives, see refs 71a-f. (a) Sebald, A.; Wrackmeyer, B. Spectrochim. Acta, Part A 1981, 37A, 365-368.
  • 89
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    • For studies of 1JC-C on metal complexes in general, see ref 69, pp 186-196. For dramatic differences between mono- and dinuclear alkynemetal complexes, see in particular: Aime, S, Osella, D, Giamello, E, Granozzi, G. J. Organomet. Chem. 1984, 262, C1-C4
    • C-C on metal complexes in general, see ref 69, pp 186-196. For dramatic differences between mono- and dinuclear alkynemetal complexes, see in particular: Aime, S.; Osella, D.; Giamello, E.; Granozzi, G. J. Organomet. Chem. 1984, 262, C1-C4.
  • 92
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    • The identity of the trans-ligand in (ha1o)(13C 13CH2)Rh[(i-Pr)3P]2 affects 1JC-C; see ref 48. Apparently, in ref 48 the reported values of 1JC-C are off by a factor of 2
    • C-C are off by a factor of 2.
  • 108
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    • In other applications of heterocyclic phosphines the steric hindrance at the basic nitrogen is quite important,32 but as seen in calculated structures here, there is no evidence of the involvement of basic nitrogen in alkyne-to-vinylidene transformation on RhI, Therefore, we feel that lack of a ring tert-butyl substituent in calculated species should be of little consequence
    • 32 but as seen in calculated structures here, there is no evidence of the involvement of basic nitrogen in alkyne-to-vinylidene transformation on Rh(I). Therefore, we feel that lack of a ring tert-butyl substituent in calculated species should be of little consequence.
  • 116
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    • Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003. For complete reference, see Supporting Information.
    • Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003. For complete reference, see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.