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Volumn , Issue 6, 1997, Pages 1221-1234

Direct evidence for anchimeric assistance in alcohol elimination from gas-phase MH+ ions of 1,4-dialkoxycyclohexanes under chemical ionisation. Experiment and theory

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EID: 0346508263     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605638e     Document Type: Article
Times cited : (16)

References (43)
  • 1
    • 0346508572 scopus 로고
    • ed. H. Kagan, Thieme, Stuttgart, and references cited therein
    • A. Mandelbaum, in Stereochemistry, ed. H. Kagan, Thieme, Stuttgart, 1977, vol. 1, p. 138, and references cited therein.
    • (1977) Stereochemistry , vol.1 , pp. 138
    • Mandelbaum, A.1
  • 8
    • 0003467672 scopus 로고
    • Wiley, New York, and references cited therein
    • J. March, Advanced Organic Chemistry, 4th edn., Wiley, New York, 1992, pp. 308-320 and references cited therein.
    • (1992) Advanced Organic Chemistry, 4th Edn. , pp. 308-320
    • March, J.1
  • 10
    • 33845557891 scopus 로고
    • Related anchimerically assisted bimolecular substitution reactions in gas-phase ions have been reported under radiolytic conditions: (a) G. Angelini and M. Speranza, J. Am. Chem. Soc., 1981, 81, 3792; (b) G. Angelini and M. Speranza, J. Am. Chem. Soc., 1981, 81, 3800.
    • (1981) J. Am. Chem. Soc. , vol.81 , pp. 3792
    • Angelini, G.1    Speranza, M.2
  • 11
    • 33845558545 scopus 로고
    • Related anchimerically assisted bimolecular substitution reactions in gas-phase ions have been reported under radiolytic conditions: (a) G. Angelini and M. Speranza, J. Am. Chem. Soc., 1981, 81, 3792; (b) G. Angelini and M. Speranza, J. Am. Chem. Soc., 1981, 81, 3800.
    • (1981) J. Am. Chem. Soc. , vol.81 , pp. 3800
    • Angelini, G.1    Speranza, M.2
  • 34
    • 0014096890 scopus 로고
    • An NMR study showed that in solution the diaxial: diequatorial conformers concentration ratio was 15:85 in pyridine and 2:98 in water: W. F. Trager, B. J. Nist and A. C. Huitric, J. Pharm. Sci., 1967, 56, 698.
    • (1967) J. Pharm. Sci. , vol.56 , pp. 698
    • Trager, W.F.1    Nist, B.J.2    Huitric, A.C.3
  • 39
    • 0347274860 scopus 로고
    • -1) for the conversion of the chair conformation of cyclohexane to the twisted boat conformation than we calculated for the conversion of diax-10t to 14. We believe that this is due to the stabilisation of TS3 relative to diax-10t by the more favourable electrostatic interaction between the positively charged carbon and the 4-hydroxy group in the developing twist-boat conformation of TS3.
    • (1990) J. Phys. Chem. , vol.94 , pp. 5630
    • Dixon, D.A.1    Komornicki, A.2
  • 40
    • 0346508568 scopus 로고    scopus 로고
    • note
    • 17 serves as a model for estimating more accurately the effects operating in these protonated 4-methoxycyclohexanols. In the CIMS experiment preferential protonation will occur at the methoxy group, which has a higher proton affinity.


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