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Volumn 133, Issue 40, 2011, Pages 15918-15921

Ethylene-promoted versus ethylene-free enyne metathesis

Author keywords

[No Author keywords available]

Indexed keywords

ENYNE METATHESIS; GRUBBS CATALYSTS; INERT ATMOSPHERES; MALDI-TOF; MASS SPECTRA; RING CLOSINGS;

EID: 80053502865     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja207388v     Document Type: Article
Times cited : (44)

References (40)
  • 2
    • 77954305294 scopus 로고    scopus 로고
    • Mori, M. Materials 2010, 3, 2087-2140
    • (2010) Materials , vol.3 , pp. 2087-2140
    • Mori, M.1
  • 12
    • 17744383192 scopus 로고    scopus 로고
    • and to faster turnover by reaction of ethylene, vs enyne, as discussed below (see
    • Galan, B. R.; Giessert, A. J.; Keister, J. B.; Diver, S. T. J. Am. Chem. Soc. 2005, 127, 5762-5763) and to faster turnover by reaction of ethylene, vs enyne, as discussed below (see
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5762-5763
    • Galan, B.R.1    Giessert, A.J.2    Keister, J.B.3    Diver, S.T.4
  • 20
    • 0033614857 scopus 로고    scopus 로고
    • Consistent with this concentration-dependence is behaviour observed by Hoye and co-workers, who recognized in early, ethylene-free work that the ene-first mechanism (see later) necessitates reaction with incoming enyne to liberate the diene product, and therefore proposed that increased enyne concentrations might be beneficial. Conversions were indeed dramatically improved by slow addition of Ru-1 to enyne, but yields suffered. These reaction conditions promote the formation of oligomers. See
    • Consistent with this concentration-dependence is behaviour observed by Hoye and co-workers, who recognized in early, ethylene-free work that the ene-first mechanism (see later) necessitates reaction with incoming enyne to liberate the diene product, and therefore proposed that increased enyne concentrations might be beneficial. Conversions were indeed dramatically improved by slow addition of Ru-1 to enyne, but yields suffered. These reaction conditions promote the formation of oligomers. See: Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277-279
    • (1999) Org. Lett. , vol.1 , pp. 277-279
    • Hoye, T.R.1    Donaldson, S.M.2    Vos, T.J.3
  • 25
    • 0037189229 scopus 로고    scopus 로고
    • We observe no such behaviour at room temperature (see, for example, the rate curves for RCEYM via Ru-4 in the Supporting Information).
    • Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441-4449). We observe no such behaviour at room temperature (see, for example, the rate curves for RCEYM via Ru-4 in the Supporting Information).
    • (2002) J. Org. Chem. , vol.67 , pp. 4441-4449
    • Poulsen, C.S.1    Madsen, R.2
  • 28
    • 0042390682 scopus 로고    scopus 로고
    • The overall process of enyne metathesis can be reversed under some conditions, however. See
    • The overall process of enyne metathesis can be reversed under some conditions, however. See: Lee, H.-Y.; Kim, B. G.; Snapper, M. L. Org. Lett. 2003, 5, 1855-1858
    • (2003) Org. Lett. , vol.5 , pp. 1855-1858
    • Lee, H.-Y.1    Kim, B.G.2    Snapper, M.L.3
  • 40
    • 0000340818 scopus 로고    scopus 로고
    • RCEYM yields were previously shown to be improved by increasing propargylic substitution for reactions under ethylene. See
    • RCEYM yields were previously shown to be improved by increasing propargylic substitution for reactions under ethylene. See: Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678-693
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 678-693
    • Kitamura, T.1    Sato, Y.2    Mori, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.