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Volumn 63, Issue 26, 1998, Pages 9904-9909

Ring-closing metathesis in methanol and water

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENE DERIVATIVE; METHANOL; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG; WATER;

EID: 0032567497     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981678o     Document Type: Article
Times cited : (149)

References (60)
  • 1
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews on ROM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 14
    • 33847520251 scopus 로고    scopus 로고
    • Alkylidene 1 is inactive in polar, aprotic solvents such as DMSO and DMF.
    • Alkylidene 1 is inactive in polar, aprotic solvents such as DMSO and DMF.
  • 22
    • 0001847655 scopus 로고    scopus 로고
    • For general references on solid supported ROM, see: (a) Peters, J.-U.; Blechert, S. Synlett. 1997, 348-350.
    • (1997) Synlett. , pp. 348-350
    • Peters, J.-U.1    Blechert, S.2
  • 28
    • 0029975056 scopus 로고    scopus 로고
    • For general reviews of other carbon-carbon bond forming processes in water, see: (a) Li, C. J. Tetrahedron 1996,52,5643-5668.
    • (1996) Tetrahedron , pp. 5643-5668
    • Li, C.J.1
  • 34
    • 20644443971 scopus 로고
    • Ph.D. Thesis, California Institute of Technology
    • Novak, B. M. Ph.D. Thesis, California Institute of Technology, 1989.
    • (1989)
    • Novak, B.M.1
  • 38
    • 33847509883 scopus 로고    scopus 로고
    • In certain cases, the use of 5 mol % 2 in the RCM of 4 gives up to 5% product. The use of alkylidene 3 or increased loading of alkylidene 2 affords no increase in conversion
    • In certain cases, the use of 5 mol % 2 in the RCM of 4 gives up to 5% product. The use of alkylidene 3 or increased loading of alkylidene 2 affords no increase in conversion.
  • 39
    • 0001263185 scopus 로고
    • and references therein
    • Fu, G. C.; Grubbs, K. H. J. Am. Chem. Soc. 1992, 114, 5426-5427, and references therein.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5426-5427
    • Fu, G.C.1    Grubbs, K.H.2
  • 42
    • 33847528553 scopus 로고    scopus 로고
    • John Wiley and Sons: New York, 2nd ed.
    • For a general procedure for malonate alkylation, see: Gilman, H.; Blatt, A. H. Organic Syntheses, Coll. Vol. I; John Wiley and Sons: New York, 2nd ed., 250-251.
    • Organic Syntheses, Coll. , vol.1 , pp. 250-251
    • Gilman, H.1    Blatt, A.H.2
  • 43
    • 0001609007 scopus 로고
    • and references therein
    • For a discussion of the effects of substrate homologation on intramolecular cyclizations, see: Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232 and references therein.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 224-232
    • Jung, M.E.1    Gervay, J.2
  • 44
    • 33847530627 scopus 로고    scopus 로고
    • Another factor that should be considered is substrate dimerization, but this does not appear to be significant in the RCM of 10 as conversion is not dependent on substrate concentration
    • Another factor that should be considered is substrate dimerization, but this does not appear to be significant in the RCM of 10 as conversion is not dependent on substrate concentration.
  • 45
    • 20644466496 scopus 로고    scopus 로고
    • note
    • In the synthesis of unsymmetrical olefins with this methodology, it is critical that the phenyl substituent be placed on the more substituted olefin as in substrate 11. If the phenyl substituent is placed on the less substituted olefin, the ruthenium carbene will preferentially react with the 1,2-disubstituted olefin, then react with the gemdisubstituted olefin intramolecularly, giving one equivalent of cyclized product and the unstable methylidene.
  • 46
    • 20644460864 scopus 로고    scopus 로고
    • note
    • 3-. See ref 16.
  • 59
    • 33847506679 scopus 로고    scopus 로고
    • 1H NMR. This did not affect the behavior of 11 and was discounted
    • 1H NMR. This did not affect the behavior of 11 and was discounted.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.