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Volumn 24, Issue 13, 2005, Pages 3172-3181

Theoretical investigation on the mechanisms of the PtCl 2-mediated cycloisomerization of polyfunctionalized 1,6-enynes. 1. Role of the propargylic substituants

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ESTERS; ISOMERIZATION; MOLECULAR DYNAMICS; OXIDATION; PLATINUM COMPOUNDS; POSITIVE IONS; POTENTIAL ENERGY; REACTION KINETICS;

EID: 21644450531     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050131e     Document Type: Article
Times cited : (55)

References (130)
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    • Fürstner, A., Ed.; Springer-Verlag: Berlin
    • (b) Mori, M. In Topics in Organometallic Chemistry, Fürstner, A., Ed.; Springer-Verlag: Berlin, 1998; Vol. 1, p 133.
    • (1998) Topics in Organometallic Chemistry , vol.1 , pp. 133
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  • 81
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    • note
    • 6 in 11).
  • 85
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    • note
    • 22a
  • 86
    • 23144452906 scopus 로고    scopus 로고
    • note
    • Further details are provided in the Suppoting Information.
  • 88
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    • note
    • 29
  • 89
    • 23144447542 scopus 로고    scopus 로고
    • note
    • 13a,29
  • 103
    • 0000597682 scopus 로고    scopus 로고
    • The related Simmons-Smith cyclopropanation of zinc carbenoid species also takes place through a direct carbene insertion: (a) Dargel, T. K.; Koch, W. J. Chem. Soc., Perkin Trans. 2 1996, 877-881.
    • (1996) J. Chem. Soc., Perkin Trans. 2 , pp. 877-881
    • Dargel, T.K.1    Koch, W.2
  • 108
    • 23144459166 scopus 로고    scopus 로고
    • note
    • 1-Pt-Cl is 38.9 and 94.4° in 13 vs 8.2 and 11.6° in 22.
  • 109
    • 0034816899 scopus 로고    scopus 로고
    • (a) These bond lengths contrast with other results that indicate an early transition structure for concerted cyclopropanation from metal-carbene, such that found for intermolecular cyclopropanation of the Cud) carbene complex: Fraile, J. M.; García, J. I.; Martínez-Merino, V.; Mayoral, J. M.; Salvatella, L. J. Am. Chem. Soc. 2001, 123, 7616-7625.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7616-7625
    • Fraile, J.M.1    García, J.I.2    Martínez-Merino, V.3    Mayoral, J.M.4    Salvatella, L.5
  • 110
    • 23144452130 scopus 로고    scopus 로고
    • note
    • (b) For the related Simmons-Smith cyclopropanation of Zn(II) carbenoid species, see ref 43.
  • 111
    • 0041588921 scopus 로고
    • For previous theoretical works about formation of cyclopropanes from transition-metal carbene complexes and alkenes, see: (a) Jaeger, M.; Prosenc, M. H.; Sontag, C.; Fischer, H. New J. Chem. 1995, 19, 911-919.
    • (1995) New J. Chem. , vol.19 , pp. 911-919
    • Jaeger, M.1    Prosenc, M.H.2    Sontag, C.3    Fischer, H.4
  • 114
    • 0001007915 scopus 로고    scopus 로고
    • A variety of explanations based on hyperconjugative interactions at the transition state and various orbital mixing/tilting effects have been provided to explain the control of diastereoselectivity during additions to unsaturated groups, (a) Mehta, G.; Chandrasekhar, J. Chem. Rev. 1999, 99, 1437-1468.
    • (1999) J. Chem. Rev. , vol.99 , pp. 1437-1468
    • Mehta, G.1    Chandrasekhar2


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