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Volumn 118, Issue 44, 1996, Pages 10904-10905

The role of iodotrimethylsilane in the conjugate addition of butylcopper·lithium iodide to α-enones; silylation of an intermediate π-complex

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE;

EID: 0029798677     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962122q     Document Type: Article
Times cited : (20)

References (33)
  • 12
    • 0345565976 scopus 로고
    • (b) Ibid. 1981, 37, 1385.
    • (1981) Tetrahedron , vol.37 , pp. 1385
  • 21
    • 10544251537 scopus 로고    scopus 로고
    • note
    • The preparative procedure uses more concentrated reaction mixtures (ca. 0.2-0.3 M) and a slight excess of reagent. See ref 10 for a representative procedure.
  • 23
    • 10544249068 scopus 로고    scopus 로고
    • note
    • The fact that the yield of 3 does not significantly increase after the initial 4 s could indicate that a complex between TMSI and the carbonyl oxygen of the enone is an important event in the rate-determining step. See also ref 6.
  • 27
    • 0542430100 scopus 로고
    • The small but increasing amounts of 2 in the reaction mixtures may be due to cleavage of 3 by TMSI. See: Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761.
    • (1977) J. Org. Chem. , vol.42 , pp. 3761
    • Jung, M.E.1    Lyster, M.A.2
  • 30
    • 10544251159 scopus 로고    scopus 로고
    • note
    • 2CuLi·LiI in THF with 1 or 2 equiv of TMSCl give mainly TMS enol ether. Private communication with Dr. Steven Bertz.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.