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Volumn 31, Issue 24, 1990, Pages 3381-3384

Diels-alder reactions: Rate acceleration promoted by a biphenylenediol

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE;

EID: 0025281206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)97402-1     Document Type: Article
Times cited : (159)

References (30)
  • 3
    • 0001341895 scopus 로고
    • For the use of an intramolecular hydrogen bond to induce facial selectivity within a dienophile see
    • (1983) J. Org. Chem. , vol.48 , pp. 1137
    • Choy1    Reed2    Masamune3
  • 4
    • 0017765837 scopus 로고
    • Regiochemical control in the Diels-Alder reactions of substituted naphthoquinones. Model studies on a regiospecific approach to adriamycinone
    • For the regiochemical effects of intramolecular hydrogen bending see, inter alia, and references therein
    • (1977) Journal of the American Chemical Society , vol.99 , pp. 5513
    • Kelly1    Gillard2    Goerner3    Lyding4
  • 5
    • 84918601485 scopus 로고    scopus 로고
    • 5 for Diels-Alder reactions conducted in water and in the presence of cyclodextrins that are attributed to hydrophobic effects may be at least partially due to hydrogen bonding.
  • 20
    • 84918614225 scopus 로고    scopus 로고
    • 3) data for new compounds. 11: 87–88°C, δ 4.42–4.56 (m, 4H), 5.05–5.20 (m, 4H), 5.78–5.96 (m, 2H), 6.92 (dd, J=1.6 & 8.0 Hz, 2H), 7.05 (t, J=8.0 Hz, 2H), 7.54 (dd, J=1.6 & 8.0 Hz, 2H); 12: 103–104°C, δ 3.44 (bd, J=4.8 Hz, 4H), 4.86 (s, 2H), 5.08–5.25 (m, 4H), 5.90–6.16 (m, 2H), 7.00 (d, J=8.0 Hz, 2H), 7.53 (d, J=8.0 Hz, 2H); 13: δ 0.98 (t, J=6.0 Hz, 6H), 1.58–1.78 (m, 4H), 2.50–2.72 (m, 4H), 4.73 (s, 2H), 7.00 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 2H); 14:δ 1.00 (t, J=6.0 Hz, 6H), 1.50–1.90 (m, 4H), 2.50–2.85 (m, 4H), 5.45 (bs, 2H), 7.90 (s, 2H); 15: 104–105°C, δ 0.86 (t, J=6.0 Hz, 6H), 1.45–1.64 (m, 4H), 2.44–2.68 (m, 4H), 4.65 (d, J=12.0 Hz, 2H), 4.80 (d, J=12.0 Hz, 2H), 6.88–6.97 (m, 4H), 7.15–7.24 (m, 6H), 7.65 (s, 2H); 16: [[Truncated]]
  • 21
    • 84918644220 scopus 로고    scopus 로고
    • 13–17 samples) were taken to measure the extent of product formation. Catalyst 8 was recovered in most of the cases by preparative tlc separation.
  • 28
    • 84918647155 scopus 로고
    • have reported that some phenols accelerate the Diels-Alder reaction between p-benzoquinone and cyclopentadiene but they suggest involvement of an electron transfer process.
    • (1949) J. Chem. Soc. , pp. 3046
    • Wasserman1    Rubin2    Steiner3    Wasserman4
  • 29
    • 84918607386 scopus 로고    scopus 로고
    • a's of putative catalysts and their effectiveness: picric acid and acetic acid are inferior to p-nitrophenol as catalysts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.