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Volumn , Issue 11, 2007, Pages 1671-1674

Al/PbCl2-catalyzed DMF-mediated reductive coupling of Baylis-Hillman acetates with tetrachloromethane

Author keywords

Baylis Hillman acetate; Catalytic system; Reductive coupling; Tetrachloromethane

Indexed keywords

ALKANOIC ACID; ALKENE; ALUMINUM CHLORIDE; CARBON TETRACHLORIDE; LEAD CHLORIDE; METHYL 3 ACETOXY 3 PHENYL 2 METHYLENEPROPANOIC ACID; N,N DIMETHYLFORMAMIDE; PROPIONIC ACID; UNCLASSIFIED DRUG;

EID: 34447556703     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984507     Document Type: Article
Times cited : (5)

References (63)
  • 8
    • 34447525743 scopus 로고
    • Additions to C-X π-Bonds In Comprehensive
    • Schreiber, S. L, Ed, Pergamon Press: Oxford
    • (a) Kelly, S. E. Additions to C-X π-Bonds In Comprehensive Organic Synthesis, Part 1; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991.
    • (1991) Organic Synthesis , Issue.PART 1
    • Kelly, S.E.1
  • 52
    • 0001420970 scopus 로고    scopus 로고
    • 1H NMR spectrum of a trisubstituted alkene the β-vinylic protons, cis and trans to the ester group, are known to resonate at around δ = 7.5 and 6.5 ppm, respectively, when the alkene is substituted by an aryl group; while the same proton cis and trans to an ester group appears at around δ = 6.8 and 5.7 ppm, respectively, when substituted by an alkyl group. See: (a) Larson, G. L.; de Kaifer, C. F.; Seda, R.; Torres, L. E.; Ramirez, J. R. J. Org. Chem. 1984, 49, 3385.
    • 1H NMR spectrum of a trisubstituted alkene the β-vinylic protons, cis and trans to the ester group, are known to resonate at around δ = 7.5 and 6.5 ppm, respectively, when the alkene is substituted by an aryl group; while the same proton cis and trans to an ester group appears at around δ = 6.8 and 5.7 ppm, respectively, when substituted by an alkyl group. See: (a) Larson, G. L.; de Kaifer, C. F.; Seda, R.; Torres, L. E.; Ramirez, J. R. J. Org. Chem. 1984, 49, 3385.
  • 62
    • 34447499224 scopus 로고    scopus 로고
    • 4. After evaporation of the solvent, the residue was purified by chromatography using cyclohexane-EtOAc (6:1) as eluent to give pure 2.
    • 4. After evaporation of the solvent, the residue was purified by chromatography using cyclohexane-EtOAc (6:1) as eluent to give pure 2.
  • 63
    • 34447502602 scopus 로고    scopus 로고
    • Data for Compounds 2 Compound(E)-2a: 1H NMR (400 MHz, CDCl3, δ, 3.85 (s, 3 H, OCH3, 4.17 (s, 2 H, CH2, 7.32-7.39 (m, 5 H, ArH, 7.94 (s, 1 H, ArCH, 13C NMR (100 MHz, CDCl3, δ, 49.56, 52.32, 98.27, 126.66, 128.69, 128.84, 128.92, 134.88, 144.85, 168.27. IR (film, ν, 3060, 3028, 2952, 1724, 1633, 1577 cm-1. MS (70 eV, m/z, 292 [M, Anal. Calcd for C12H11Cl 3O2: C, 49.09; H, 3.78. Found: C, 49.38; H, 3.74. Compound (E)-2b: 1H NMR (400 MHz, CDCl3, δ, 2.37 (s, 3 H, CH3, 3.86 (s, 3 H, OCH3, 4.19 (s, 2 H, CH2, 7.21 (d, 2 H, J, 8.0 Hz, ArH, 7.35 (d, 2 H, J, 8.0 Hz, ArH, 7.91 (s, 1 H, ArCH, 13C NMR 100 MHz, CDCl 3, δ, 21.30, 49.74, 52.31,98.48,125.76,129.14,129.46,131.97, 139.3
    • 2: C, 42.57; H, 2.98. Found: C, 42.33; H, 2.95...


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.