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Volumn 68, Issue 2, 2003, Pages 216-226

Stable simple enols. Resolution of chiral 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylethenol. A different racemization mechanism for the enol and its acetate

Author keywords

[No Author keywords available]

Indexed keywords

RACEMIZATION;

EID: 0037462372     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020497q     Document Type: Article
Times cited : (14)

References (33)
  • 1
    • 0001176011 scopus 로고    scopus 로고
    • Seoul, Korea, August 25-29
    • th IUPAC Conference on Physical Organic Chemistry, Seoul, Korea, August 25-29, 1996; Rappoport, Z.; Frey, Y.; Sigalov, M.; Rochlin, E. Pure Appl. Chem. 1997, 69, 1933.
    • (1996) th IUPAC Conference on Physical Organic Chemistry
  • 17
    • 0346351352 scopus 로고    scopus 로고
    • note
    • ‡ = -18.5 eu which is inconsistent with a monomolecular ring-flip process.
  • 20
    • 0004210270 scopus 로고    scopus 로고
    • Wiley: Chichester
    • Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. R. Vinyl Cations, Academic Press: New York, 1979; Rappoport, Z.; Stang, P. J. Dicoordinated Carbocations, Wiley: Chichester, 1997.
    • (1997) Dicoordinated Carbocations
    • Rappoport, Z.1    Stang, P.J.2
  • 21
    • 6244260514 scopus 로고
    • + ion. Hence, neglecting other effects, C1 protonation, leading to 18, and C2 protonation have close probabilities. It is difficult to evaluate the contributions of the combined additional stabilization by the OH and destabilization by the 2-F in the C2 protonated ion, the different electron withdrawal by the β-groups in both cations and the lower steric effect to protonation at C1 than at C2, and the only conclusion is that protonation at C1 is a viable possibility, especially in view of the argument brought above against C2 protonation.
    • (1956) J. Chem. Soc. , pp. 850
    • Charlton, C.1    Hughes, E.D.2
  • 22
    • 0347612123 scopus 로고
    • Ph.D. Thesis. Bryn Mawr College
    • + ion. Hence, neglecting other effects, C1 protonation, leading to 18, and C2 protonation have close probabilities. It is difficult to evaluate the contributions of the combined additional stabilization by the OH and destabilization by the 2-F in the C2 protonated ion, the different electron withdrawal by the β-groups in both cations and the lower steric effect to protonation at C1 than at C2, and the only conclusion is that protonation at C1 is a viable possibility, especially in view of the argument brought above against C2 protonation.
    • (1957)
    • Shieh, N.1
  • 23
    • 0346981222 scopus 로고
    • + ion. Hence, neglecting other effects, C1 protonation, leading to 18, and C2 protonation have close probabilities. It is difficult to evaluate the contributions of the combined additional stabilization by the OH and destabilization by the 2-F in the C2 protonated ion, the different electron withdrawal by the β-groups in both cations and the lower steric effect to protonation at C1 than at C2, and the only conclusion is that protonation at C1 is a viable possibility, especially in view of the argument brought above against C2 protonation.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 7041
    • Rappoport, Z.1    Shulman, P.2    Thuval Shoolman, M.3
  • 24
    • 0036605559 scopus 로고    scopus 로고
    • + ion. Hence, neglecting other effects, C1 protonation, leading to 18, and C2 protonation have close probabilities. It is difficult to evaluate the contributions of the combined additional stabilization by the OH and destabilization by the 2-F in the C2 protonated ion, the different electron withdrawal by the β-groups in both cations and the lower steric effect to protonation at C1 than at C2, and the only conclusion is that protonation at C1 is a viable possibility, especially in view of the argument brought above against C2 protonation.
    • (2002) J. Phys. Org. Chem. , vol.15 , pp. 330
    • Fujio, M.1    Kim, H.-J.2    Uddin, M.K.3    Yoh, S.-D.4    Rappoport, Z.5    Tsuno, Y.6
  • 26
    • 0002502815 scopus 로고
    • Rappoport, Z. Ed., Wiley: Chichester; Chapter 7
    • Keeffe J. R.; Kresge, A. J. In The Chemistry of Enols; Rappoport, Z. Ed., Wiley: Chichester, 1990; Chapter 7, pp 434-446.
    • (1990) The Chemistry of Enols , pp. 434-446
    • Keeffe, J.R.1    Kresge, A.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.