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Volumn 118, Issue 17, 1996, Pages 4194-4195

NMR spectroscopic evidence for π-complexation and the formation of a vinylcopper intermediate in the reaction between methyl phenylpropiolate andtBuCu(CN)Li

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Indexed keywords

COPPER COMPLEX;

EID: 0029901510     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953676g     Document Type: Article
Times cited : (40)

References (30)
  • 1
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    • (1992) Org. React. , vol.41 , pp. 135
    • Lipshutz, B.H.1    Sengupta, S.2
  • 4
    • 33748240379 scopus 로고
    • Recent examples: (a) Snyder, J. P. Angew Chem., Int. Ed. Engl. 1995, 34, 80. (b) Dorigo, A. E., Wanner, J.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 476. Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025.
    • (1995) Angew Chem., Int. Ed. Engl. , vol.34 , pp. 80
    • Snyder, J.P.1
  • 6
    • 0000647642 scopus 로고
    • Recent examples: (a) Snyder, J. P. Angew Chem., Int. Ed. Engl. 1995, 34, 80. (b) Dorigo, A. E., Wanner, J.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 476. Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11025
    • Snyder, J.P.1
  • 14
    • 0001815350 scopus 로고
    • Copper acetylene π-complexes are well studied in the solid state: (a) Reger, D. L.; Huff, M. F. Organometallics 1992, 11, 69. (b) Brantin, K.; Håkansson, M.; Jagner, S. J. Organomet. Chem. 1994, 474, 229 and references cited therein.
    • (1992) Organometallics , vol.11 , pp. 69
    • Reger, D.L.1    Huff, M.F.2
  • 15
    • 0000792088 scopus 로고
    • and references cited therein
    • Copper acetylene π-complexes are well studied in the solid state: (a) Reger, D. L.; Huff, M. F. Organometallics 1992, 11, 69. (b) Brantin, K.; Håkansson, M.; Jagner, S. J. Organomet. Chem. 1994, 474, 229 and references cited therein.
    • (1994) J. Organomet. Chem. , vol.474 , pp. 229
    • Brantin, K.1    Håkansson, M.2    Jagner, S.3
  • 17
    • 4243124152 scopus 로고
    • (b) Several examples of electrophiles: Hall, D. G.; Chapdelaine, D.; Preville, P.; Deslongchamps. P. Syrden 1994, 660. (c) TMSCl: Marino, J. P., Linderman, R. J. J. Org. Chem. 1981, 46, 3696. Fleming, I.; Perry, D. A. Tetrahedron 1981, 37, 4027.
    • (1994) Syrden , pp. 660
    • Hall, D.G.1    Chapdelaine, D.2    Preville, P.3    Deslongchamps, P.4
  • 18
    • 33845556090 scopus 로고
    • (b) Several examples of electrophiles: Hall, D. G.; Chapdelaine, D.; Preville, P.; Deslongchamps. P. Syrden 1994, 660. (c) TMSCl: Marino, J. P., Linderman, R. J. J. Org. Chem. 1981, 46, 3696. Fleming, I.; Perry, D. A. Tetrahedron 1981, 37, 4027.
    • (1981) J. Org. Chem. , vol.46 , pp. 3696
    • Marino, J.P.1    Linderman, R.J.2
  • 19
    • 0001536288 scopus 로고
    • (b) Several examples of electrophiles: Hall, D. G.; Chapdelaine, D.; Preville, P.; Deslongchamps. P. Syrden 1994, 660. (c) TMSCl: Marino, J. P., Linderman, R. J. J. Org. Chem. 1981, 46, 3696. Fleming, I.; Perry, D. A. Tetrahedron 1981, 37, 4027.
    • (1981) Tetrahedron , vol.37 , pp. 4027
    • Fleming, I.1    Perry, D.A.2
  • 24
    • 85086525785 scopus 로고    scopus 로고
    • note
    • 2 218,130680. Found: 218.130659.
  • 25
    • 85086528288 scopus 로고    scopus 로고
    • note
    • 4 (δ = 0.0). The observed shift for the Bu-cyanocuprate in the reaction mixture was -0.67 ppm.
  • 29
    • 4243194789 scopus 로고    scopus 로고
    • note
    • 2.3 = -62.2.
  • 30
    • 4243201631 scopus 로고    scopus 로고
    • note
    • After the NMR sample was kept for several days in a freezer at -20°C. no characteristic peaks assignable to an adduct could be observed.


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