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Volumn 71, Issue 21, 2006, Pages 8250-8255

Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations

Author keywords

[No Author keywords available]

Indexed keywords

ENOLS; REACTIVITY; TRANSITION STATE;

EID: 33750005591     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061450y     Document Type: Article
Times cited : (10)

References (46)
  • 21
    • 0004123611 scopus 로고
    • Wiley-Interscience: New York
    • For a review and a wide ranging discussion of simple enols, see: Rappoport, Z. The Chemistry of Enols; Wiley-Interscience: New York, 1990.
    • (1990) The Chemistry of Enols
    • Rappoport, Z.1
  • 31
    • 0013082201 scopus 로고
    • Vinyl acetals are known to undergo intial acetal hydrolysis to release the enol, followed by ketonization; see: Chiang, Y.; Chwang, W. K.; Kresge, A. J.; Yin, Y. J. Am. Chem. Soc. 1989, 111, 7185.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7185
    • Chiang, Y.1    Chwang, W.K.2    Kresge, A.J.3    Yin, Y.4
  • 34
    • 33644595381 scopus 로고    scopus 로고
    • Tidwell has recently described a transition structure in which six water molecules link the α-carbon to an intramolecular basic group: Fedorov, A. V.; Najafian, K.; Tidwell, T. T.; Vukovic, S. Can. J. Chem. 2005, 83, 1561.
    • (2005) Can. J. Chem. , vol.83 , pp. 1561
    • Fedorov, A.V.1    Najafian, K.2    Tidwell, T.T.3    Vukovic, S.4
  • 35
    • 0037533809 scopus 로고    scopus 로고
    • For a description of this effect of this destabilisation on rearrangement reactions: Black, K. A.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 6715.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6715
    • Black, K.A.1    Wilsey, S.2    Houk, K.N.3
  • 38
    • 1942489246 scopus 로고    scopus 로고
    • (b) For a recent description of this effect during the enolization of hydroxyacetone, see: Crugieras, J.; Richard, J. P. J. Am. Chem. Soc. 2004, 126, 5164.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5164
    • Crugieras, J.1    Richard, J.P.2
  • 39
    • 0037899651 scopus 로고    scopus 로고
    • (c) For a computational study of the deprotonation of fluoroacetyl SCoA by citrate synthase, see: Yang, W.; Drueckhammer, D. G. J. Phys. Chem. B 2003, 107, 5986.
    • (2003) J. Phys. Chem. B , vol.107 , pp. 5986
    • Yang, W.1    Drueckhammer, D.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.