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Volumn 70, Issue 25, 2005, Pages 10247-10259

1-Bromo-1-lithioethene: A practical reagent in organic synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHELATION; CRYSTAL STRUCTURE; ELECTRON TRAPS; KETONES; SYNTHESIS (CHEMICAL);

EID: 28744434075     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051125v     Document Type: Article
Times cited : (13)

References (86)
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    • (2002) Cross-Coupling Reactions - A Practical Guide , vol.219
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    • Heaney, H.1    Christie, S.2
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    • (1994) Organocopper Reagents
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    • 0021915012 scopus 로고
    • For an example of bromohydroxylation/amination en route to α-methylene-γ-lactams, see: Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375-385.
    • (1985) Tetrahedron , vol.41 , pp. 375-385
    • Mori, M.1    Chiba, K.2    Okita, M.3    Kayo, I.4    Ban, Y.5
  • 20
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    • As a source of functionalized vinyllithium and vinylcuprate reagents, see: Cloninger, M. J.; Overman, L.-E. J. Am. Chem. Soc. 1999, 121, 1092-1093.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1092-1093
    • Cloninger, M.J.1    Overman, L.-E.2
  • 23
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    • (d) For an example of oxidation to α-bromo enones, see: Della, E. W.; Pigou, P. E. Aust. J. Chem. 1983, 36, 2261-2268.
    • (1983) Aust. J. Chem. , vol.36 , pp. 2261-2268
    • Della, E.W.1    Pigou, P.E.2
  • 28
    • 28744448466 scopus 로고
    • (h) For examples of dehydrobromination to the corresponding propargyl alcohol, see: Lespieau, R. C.R. Hebd. Seances Acad. Sci. 1911, 152, 879-881.
    • (1911) C.R. Hebd. Seances Acad. Sci. , vol.152 , pp. 879-881
    • Lespieau, R.1
  • 36
    • 0000936473 scopus 로고
    • 2 = Me; 50% yield), see: Sandler, S. R. J. Org. Chem. 1967, 32, 3876-3881.
    • (1967) J. Org. Chem. , vol.32 , pp. 3876-3881
    • Sandler, S.R.1
  • 48
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    • A preliminary account of some of these studies has appeared in: Novikov, Y. Y.; Sampson, P. Org. Lett. 2003, 5, 2263-2266.
    • (2003) Org. Lett. , vol.5 , pp. 2263-2266
    • Novikov, Y.Y.1    Sampson, P.2
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    • 28744456223 scopus 로고    scopus 로고
    • note
    • The Trapp mixture is THF, ether, and pentane (4:1:1 by volume). This mixture has a sufficiently low viscosity at -110 to -115 °C to provide a useful reaction medium.
  • 58
    • 28744452983 scopus 로고    scopus 로고
    • note
    • Of course, the α-anomer would suffer increased steric crowding on the α-face, which might have eroded this high stereocontrol; unfortunately, no studies along these lines have been published.
  • 61
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    • For reviews on the use of acylsilanes in organic synthesis, see: (a) Ricci, A.; Deglinnocenti, A. Synthesis 1989, 647-660.
    • (1989) Synthesis , pp. 647-660
    • Ricci, A.1    Deglinnocenti, A.2
  • 69
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    • note
    • A typical optimization took about 3 weeks on a desktop 2.4 GHz Pentium 4 computer with 1 GB memory; this precluded the use of an MP2 correlation correction as well as HF/DFT methods available within the GAMESOL package.
  • 74
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    • The closely related 1-bromo-1-chloroethene was mentioned in the literature (Havel, J. J.; Skell, P. S. J. Am. Chem. Soc. 1972, 94, 1792-1793.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 1792-1793
    • Havel, J.J.1    Skell, P.S.2
  • 76
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    • but it readily polymerizes and has not found utility as a synthetic reagent. In contrast, 1,1-dichloroethene is an inexpensive article of commerce, and has found some synthetic utility. For an example, see: Qian, M.; Negishi, E. Org. Process Res. Dev. 2003, 7, 412-417.
    • (2003) Org. Process Res. Dev. , vol.7 , pp. 412-417
    • Qian, M.1    Negishi, E.2
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    • note
    • The preparation of 8a is presented in the Supporting Information.
  • 83
    • 28744433347 scopus 로고    scopus 로고
    • note
    • Ketone 9a was kindly provided by Dr. Peter Norris, Department of Chemistry, Youngstown State University.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.