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Volumn 3, Issue 15, 2001, Pages 2367-2370

Study on the reactivity of the alkene component in ruthenium-catalyzed [2 + 2] cycloadditions between an alkene and an alkyne. Part 1

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ARTICLE;

EID: 0001526055     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016174i     Document Type: Article
Times cited : (54)

References (40)
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    • (b) Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 3.2, p 271.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 271
    • Chan, D.M.T.1
  • 13
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    • Liebeskind, L. S., Ed.; JAI Press: Greenwich
    • (d) Lautens, M.; Tam, W. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1998; Vol. 6, pp 49-101.
    • (1998) Advances in Metal-Organic Chemistry , vol.6 , pp. 49-101
    • Lautens, M.1    Tam, W.2
  • 14
    • 0002110351 scopus 로고    scopus 로고
    • For reviews on transition metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
    • (1996) Chem. Rev. , vol.96 , pp. 49
    • Lautens, M.1    Klute, W.2    Tam, W.3
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    • 0000167986 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford
    • Crimmins, M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 123.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 123
    • Crimmins, M.T.1
  • 26
    • 0002648396 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford
    • Baldwin, J. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 63.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 63
    • Baldwin, J.E.1
  • 33
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    • Substituted norbornadienes 2a-f were prepared according to literature procedures: (a) Story, P. R.; Fahrenholtz, S. R. J. Org. Chem. 1963, 28, 1716.
    • (1963) J. Org. Chem. , vol.28 , pp. 1716
    • Story, P.R.1    Fahrenholtz, S.R.2
  • 38
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    • note
    • 1H NMR spectra of the crude cycloaddition products. The regio- and stereochemistry of the cycloadducts were determined by various NMR techniques (NOE and GOESY experiments).
  • 40
    • 0042539782 scopus 로고    scopus 로고
    • note
    • Since different cycloadducts may provide different response from the detector of the GC, an equimolar amount of two different cycloadducts may not provide exactly a 1:1 ratio of peak areas on the GC integration. Thus, an equimolar amount of each cycloadduct was injected into the GC and their integration areas were compared. These numbers were then used to correct for the product ratios.


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