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Volumn 63, Issue 21, 1998, Pages 7183-7189

Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction

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Indexed keywords


EID: 0000516236     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980421n     Document Type: Article
Times cited : (223)

References (35)
  • 22
    • 85034194781 scopus 로고    scopus 로고
    • (+)-Binol loading was limited to 10%, as above that amount the reaction became extremely viscous and no further acceleration was observed
    • (+)-Binol loading was limited to 10%, as above that amount the reaction became extremely viscous and no further acceleration was observed.
  • 23
    • 85034202349 scopus 로고    scopus 로고
    • note
    • 3 compared to earlier rate studies is because reactions are no longer being diluted with 100 μL of MeCN. In addition, more accurate measurements are now being made. We are currently obtaining five different samples from a single reaction and analyzing them. This was not practical in the initial stages when a very large number of different reactions were conducted.
  • 24
    • 84984369829 scopus 로고
    • Hahn, F. E.; Mohr, J. Chem. Ber. 1990,123,481-484. We thank one of the reviewers for highlighting this paper to us.
    • (1990) Chem. Ber. , vol.123 , pp. 481-484
    • Hahn, F.E.1    Mohr, J.2
  • 25
    • 85034183590 scopus 로고    scopus 로고
    • It had previously been shown that 10 mol % MeOH results in a 1.5-fold rate enhancement. No further tests were conducted. See ref 10.
    • It had previously been shown that 10 mol % MeOH results in a 1.5-fold rate enhancement. No further tests were conducted. See ref 10.
  • 26
    • 85034200956 scopus 로고    scopus 로고
    • For reaction of cyclohexanecarboxaldehyde with methyl acrylate see ref 7. No yield was given, but the half-life for the reaction using 20 mol % DABCO was 10 days.
    • For reaction of cyclohexanecarboxaldehyde with methyl acrylate see ref 7. No yield was given, but the half-life for the reaction using 20 mol % DABCO was 10 days.
  • 27
    • 17144397289 scopus 로고
    • For reaction of anisaldehyde with methyl acrylate, see: Foucaud, A.; El Guemmout, F. Bull. Chim. Soc. Fr. 1989, 403-408. They reported 90% yield after 20 days using 15 mol % DABCO.
    • (1989) Bull. Chim. Soc. Fr. , pp. 403-408
    • Foucaud, A.1    El Guemmout, F.2
  • 28
    • 85034187898 scopus 로고    scopus 로고
    • Methyl acrylate has a tendency to dimerize, and with less reactive acceptors this is the major product (see refs 29 and 30). Under our optimum conditions, the rate of reaction with the aldehyde is enhanced relative to dimerization.
    • Methyl acrylate has a tendency to dimerize, and with less reactive acceptors this is the major product (see refs 29 and 30). Under our optimum conditions, the rate of reaction with the aldehyde is enhanced relative to dimerization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.