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Volumn 50, Issue 49, 2009, Pages 6787-6790

New Gilman-type lithium cuprate from a copper(II) salt: synthesis and deprotonative cupration of aromatics

Author keywords

Aromatic compound; Copper; Heterocycle; Lithium; Metalation

Indexed keywords

1,4 DIMETHOXYBENZENE; 2 BROMOPYRIDINE; 2 CHLOROPYRIDINE; 2 FLUOROPYRIDINE; 2,4 DIMETHOXYPYRIMIDINE; ANISOLE; AROMATIC COMPOUND; BENZENE DERIVATIVE; BENZENECARBONYL CHLORIDE; BUTYLLITHIUM; CHLORIDE; COPPER; COPPER DERIVATIVE; ELECTROPHILE; FURAN; IODINE; LITHIUM CUPRATE; METHYL IODIDE; NITROBENZENE; PYRIDINE DERIVATIVE; THIOPHENE; UNCLASSIFIED DRUG;

EID: 70350004076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.100     Document Type: Article
Times cited : (30)

References (63)
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    • note
    • H = 1.096 G, 2H), but was not identified:{A figure is presented}.
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    • TEMPO is similarly formed by preparing LiTMP in THF.
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    • The spectral data are analogous to those obtained from a commercial sample.
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    • 3): δ 18.6, 26.0, 31.5, 41.8, 54.4, 55.1, 111.0, 119.3, 126.4, 134.2, 136.0, 160.3.
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    • The spectral data are analogous to those previously described:. Waterlot C., Hasiak B., Couturier D., and Rigo B. Tetrahedron 57 (2001) 4889-4901
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    • The spectral data are analogous to those previously described:. Rao M.L.N., Venkatesh V., and Banerjee D. Tetrahedron 63 (2007) 12917-12926
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    • note
    • 3): δ 121.3 (d, J = 30 Hz), 121.9 (d, J = 4.5 Hz), 129.2 (s, 2C), 131.1 (d, 2C, J = 1.2 Hz), 135.0 (d, J = 0.9 Hz), 140.7 (s), 142.0 (d, J = 3.3 Hz), 150.9 (d, J = 15 Hz), 160.1 (d, J = 243 Hz), 190.7 (d, J = 4.9 Hz).
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    • note
    • 3): δ 116.7 (m), 121.7 (m), 142.0 (t, J = 3.3 Hz), 148.1 (m), 160.4 (d, J = 241 Hz).
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    • Even if the basicity of pyrimidine nitrogens is low compared with that of pyridine, competitive quaternarization by reaction with allyl bromide and methyl iodide is not impossible under the conditions used.
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    • note
    • 3): δ 54.3 (2C), 55.0 (2C), 108.3 (2C), 158.8 (2C), 165.1 (2C), 168.7 (2C).
  • 60
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    • The spectral data are analogous to those previously described:. Boudet N., Dubbaka S.R., and Knochel P. Org. Lett. 10 (2008) 1715-1718
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    • note
    • 4, filtered, and concentrated under reduced pressure before purification by column chromatography on silica gel (eluent: heptane/EtOAc 8:2). Compound 15 (0.11 g, 45%) was isolated as a yellow oil.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.