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Volumn 45, Issue 18, 2004, Pages 3547-3549

Friedel-Crafts alkylation of benzene with α,β-unsaturated amides

Author keywords

Alkylation; Aluminum chloride; Amide; Friedel Crafts; Superelectrophile

Indexed keywords

ALUMINUM CHLORIDE; AMIDE; BENZENE;

EID: 1842737315     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.067     Document Type: Article
Times cited : (23)

References (33)
  • 1
    • 1842645940 scopus 로고
    • The mechanism of these reactions involves O-protonation (coordination to a Lewis acid) of β-phenethylamides followed by electrophilic aromatic cyclialkylation. See: Olah G.A. New York: Interscience
    • The mechanism of these reactions involves O-protonation (coordination to a Lewis acid) of β-phenethylamides followed by electrophilic aromatic cyclialkylation. See: Barclay L.R.C. Olah G.A. Friedel-Crafts and Related Reactions. Vol. 2, Part 2:1964;873-937 Interscience, New York.
    • (1964) Friedel-Crafts and Related Reactions , vol.22 , pp. 873-937
    • Barclay, L.R.C.1
  • 7
    • 0000265739 scopus 로고
    • G.A. Olah, Schleyer P.R. New York: Wiley-Interscience
    • Olah G.A., White A.M., O'Brien D.H. Olah G.A., Schleyer P.R. Carbonium Ions. Vol. 4:1973;1697-1781 Wiley-Interscience, New York.
    • (1973) Carbonium Ions , vol.4 , pp. 1697-1781
    • Olah, G.A.1    White, A.M.2    O'Brien, D.H.3
  • 12
    • 0345735265 scopus 로고
    • and references cited therein
    • Johnston K.M. Tetrahedron. 24:1968;5595-5598. and references cited therein.
    • (1968) Tetrahedron , vol.24 , pp. 5595-5598
    • Johnston, K.M.1
  • 16
    • 0034704819 scopus 로고    scopus 로고
    • β-Arylcarboxylic acids (acid chlorides) have mostly been prepared by different ways as precursors and subsequently worked up with ammonia or amines. Another approach includes nucleophilic 1,4-addition of arylsiloxanes or Grignard reagents to α,β-unsaturated amides. See, for example:
    • β-Arylcarboxylic acids (acid chlorides) have mostly been prepared by different ways as precursors and subsequently worked up with ammonia or amines. Another approach includes nucleophilic 1,4-addition of arylsiloxanes or Grignard reagents to α,β-unsaturated amides. See, for example: Elz S., Kramer K., Pertz H.H., Detert H., Laak A.M., Kuhne R., Schunack W. J. Med. Chem. 43:2000;1071-1084.
    • (2000) J. Med. Chem. , vol.43 , pp. 1071-1084
    • Elz, S.1    Kramer, K.2    Pertz, H.H.3    Detert, H.4    Laak, A.M.5    Kuhne, R.6    Schunack, W.7
  • 19
    • 1842696299 scopus 로고    scopus 로고
    • U.S. Patent 5196607, 1993
    • Quallich, G. J. U.S. Patent 5196607, 1993.
    • Quallich, G.J.1
  • 20
    • 1842696295 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo to give 6 as pure individual compound.
  • 24
    • 1842746664 scopus 로고    scopus 로고
    • note
    • 13C NMR δ 35.7, 62.2, 118.7, 127, 136.3, 136.3, 143.2, 158.1, 177.2, 188.7. Quenching this acidic solution with ice provided back the starting material.
  • 28
    • 1842797168 scopus 로고    scopus 로고
    • Ref. 12, pp 295-298, 332-335
    • (a) Ref. 12, pp 295-298, 332-335.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.