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Volumn 55, Issue 11, 1990, Pages 3622-3627

Directed Lithiation of Chlorobenzenes. Regioselectivity and Application to a Short Synthesis of Benzocyclobutenes

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EID: 0001068611     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00298a045     Document Type: Article
Times cited : (63)

References (56)
  • 8
    • 85022242956 scopus 로고
    • see: (i) Wakefield, B. J. The Chemistry of Organolithium Compounds: Pergamon Press: Oxford
    • Snieckus, V. Bull. Soc. Chim. Fr. 1988, 67. For more general reviews of organolithium chemistry, see: (i) Wakefield, B. J. The Chemistry of Organolithium Compounds: Pergamon Press: Oxford, 1974.
    • (1988) Bull. Soc. Chim. Fr. , vol.67
    • Snieckus, V.1
  • 34
    • 33947296831 scopus 로고
    • For general reviews of benzocyclobutene chemistry
    • For general reviews of benzocyclobutene chemistry, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471.
    • (1970) Chem. Rev. , vol.70 , Issue.471
    • Klundt, I.L.1
  • 43
    • 2042487195 scopus 로고
    • The significance of the precoordination of the substrate electron pair to the lithiating agent for stereo- and regioselective lithiations has been reviewed
    • The significance of the precoordination of the substrate electron pair to the lithiating agent for stereo- and regioselective lithiations has been reviewed. See: Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
    • (1986) Acc. Chem. Res. , vol.19 , Issue.356
    • Beak, P.1    Meyers, A.I.2
  • 44
    • 0007659119 scopus 로고
    • For a similar example of this steric inhibition of the methoxy coordination
    • For a similar example of this steric inhibition of the methoxy coordination, see: Slocum, D. W.; Koonsvitsky, D. W. J. Org. Chem. 1973, 38, 1675.
    • (1973) J. Org. Chem. , vol.38 , pp. 1675
    • Slocum, D.W.1    Koonsvitsky, D.W.2
  • 45
    • 85022259651 scopus 로고    scopus 로고
    • Lithiation of 2-fluoroanisole occurs preferentially at the 6-position although fluorine is more electronegative than chlorine
    • Lithiation of 2-fluoroanisole occurs preferentially at the 6-position although fluorine is more electronegative than chlorine. In this case, small fluorine may not interefere with the methoxy coordination. See ref 19f.
    • In this case, small fluorine may not interefere with the methoxy coordination
  • 46
    • 0011394711 scopus 로고
    • Similar biphenyl formation from 3-fluoro-2-lithioanisole has been reported
    • Similar biphenyl formation from 3-fluoro-2-lithioanisole has been reported. See: Adejare, A.; Miller, D. D. Tetrahedron Lett. 1984, 25, 5597.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5597
    • Adejare, A.1    Miller, D.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.