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Volumn 125, Issue 31, 2003, Pages 9294-9295

A new ruthenium-catalyzed cleavage of a carbon-carbon triple bond: Efficient transformation of ethynyl alcohol into alkene and carbon monoxide

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE; ALKYNE; CARBON; CARBON MONOXIDE; DEUTERIUM; ETHYNYL ALCOHOL; FUNCTIONAL GROUP; LEWIS ACID; ORGANIC COMPOUND; RHODIUM; RUTHENIUM; UNCLASSIFIED DRUG;

EID: 0043210660     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036246w     Document Type: Article
Times cited : (118)

References (36)
  • 19
    • 0040292662 scopus 로고    scopus 로고
    • Examples for alkyne metathesis, see: (a) Furstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453. (b) Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221. (c) Bunz, U. H. F.; Kloppenberg, L. Angew. Chem., Int. Ed. 1999, 38, 478. (d) Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829. (e) Furstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734. (f) McCullough, G. L.; Shrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9453
    • Furstner, A.1    Mathes, C.2    Lehmann, C.W.3
  • 20
    • 0000406859 scopus 로고    scopus 로고
    • Examples for alkyne metathesis, see: (a) Furstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453. (b) Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221. (c) Bunz, U. H. F.; Kloppenberg, L. Angew. Chem., Int. Ed. 1999, 38, 478. (d) Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829. (e) Furstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734. (f) McCullough, G. L.; Shrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
    • (2001) Org. Lett. , vol.3 , pp. 221
    • Furstner, A.1    Mathes, C.2
  • 21
    • 0033558184 scopus 로고    scopus 로고
    • Examples for alkyne metathesis, see: (a) Furstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453. (b) Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221. (c) Bunz, U. H. F.; Kloppenberg, L. Angew. Chem., Int. Ed. 1999, 38, 478. (d) Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829. (e) Furstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734. (f) McCullough, G. L.; Shrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 478
    • Bunz, U.H.F.1    Kloppenberg, L.2
  • 22
    • 0000204261 scopus 로고    scopus 로고
    • Examples for alkyne metathesis, see: (a) Furstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453. (b) Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221. (c) Bunz, U. H. F.; Kloppenberg, L. Angew. Chem., Int. Ed. 1999, 38, 478. (d) Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829. (e) Furstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734. (f) McCullough, G. L.; Shrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
    • (2002) Org. Lett. , vol.4 , pp. 2829
    • Brizius, G.1    Bunz, U.H.F.2
  • 23
    • 0038731101 scopus 로고    scopus 로고
    • Examples for alkyne metathesis, see: (a) Furstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453. (b) Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221. (c) Bunz, U. H. F.; Kloppenberg, L. Angew. Chem., Int. Ed. 1999, 38, 478. (d) Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829. (e) Furstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734. (f) McCullough, G. L.; Shrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1734
    • Furstner, A.1    Seidel, G.2
  • 24
    • 0342847826 scopus 로고
    • Examples for alkyne metathesis, see: (a) Furstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453. (b) Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221. (c) Bunz, U. H. F.; Kloppenberg, L. Angew. Chem., Int. Ed. 1999, 38, 478. (d) Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829. (e) Furstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734. (f) McCullough, G. L.; Shrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4067
    • McCullough, G.L.1    Shrock, R.R.2
  • 36
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    • note
    • Related to this process is the water-assisted splitting of alkyne into alkane (or alkyl) and coordinated CO, which requires a stoichiometric amount of metal complexes. The latter reaction has not been effected catalytically despite its popularity and long history.


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