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Volumn 64, Issue 1, 1999, Pages 14-15

Regioselectivity of addition of organolithium reagents to enones: The role of HMPA

Author keywords

[No Author keywords available]

Indexed keywords

HEMPA; LITHIUM; ORGANOLITHIUM COMPOUND;

EID: 0033534559     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981765g     Document Type: Article
Times cited : (76)

References (39)
  • 11
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    • (f) Krief, A. Tetrahedron 1980, 36, 2531-2640.
    • (1980) Tetrahedron , vol.36 , pp. 2531-2640
    • Krief, A.1
  • 21
    • 0344149198 scopus 로고    scopus 로고
    • note
    • When the addition is reversible, higher temperatures and the addition of HMPA can favor 1, 4 addition thermodynamically: see ref 2d.
  • 22
  • 23
    • 8344271432 scopus 로고
    • (a) Hogen-Esch, T. E.; Smid, J. J. Am. Chem. Soc. 1966, 88, 307-318. Hogen-Esch, T. E. Adv. Phys. Org. Chem. 1977, 15, 153.
    • (1977) Adv. Phys. Org. Chem. , vol.15 , pp. 153
    • Hogen-Esch, T.E.1
  • 25
    • 0001332926 scopus 로고
    • A second hypothesis is that the presence of HMPA may promote a single electron transfer (SET) reaction, leading to conjugate addition. However, a mechanistic study using radical probes failed to demonstrate that this was occurring, at least in the reactions of lithiodithianes: see Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1984, 49, 935-939.
    • (1984) J. Org. Chem. , vol.49 , pp. 935-939
    • Chung, S.K.1    Dunn L.B., Jr.2
  • 26
    • 0344149197 scopus 로고    scopus 로고
    • note
    • 1e.10).
  • 32
    • 0344149195 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Wisconsin, Madison
    • Sikorski, W. H. Ph.D. Thesis, University of Wisconsin, Madison, 1997.
    • (1997)
    • Sikorski, W.H.1
  • 33
    • 0345011699 scopus 로고    scopus 로고
    • note
    • The additions were performed at -120 °C. The Supporting Information contains a description of a simple device to facilitate mixing and temperature control during low-temperature additions.
  • 34
    • 0001858861 scopus 로고    scopus 로고
    • The simulations were performed with the computer program WINDNMR (Reich, H. J. J. Chem. Educ. Software, 1996, 3D, 2).
    • (1996) J. Chem. Educ. Software , vol.3 D , pp. 2
    • Reich, H.J.1
  • 38
    • 0001424578 scopus 로고
    • Additional mechanistic complexities must appear with lithiated nitriles, which give the inverse response to solvent polarity (ether favors 1, 4 addition; THF favors 1, 2 addition). (a) Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1974, 96, 5272-5274.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5272-5274
    • Stork, G.1    Maldonado, L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.