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Volumn 69, Issue 17, 2004, Pages 5537-5546

Importance of entropy in the diastereoselectivity of 5-substituted 2-methyladamant-2-yl cations

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ELECTRONIC PROPERTIES; ENTHALPY; ENTROPY; METHANOL; POSITIVE IONS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

EID: 4043052107     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049481l     Document Type: Article
Times cited : (11)

References (40)
  • 1
    • 4043166467 scopus 로고    scopus 로고
    • For reviews on this topic, see the special issue: Chem. Rev. 1999, 99 (5): (a) Kaselji, M.; Chung, W.-S.; le Noble, W. J. Chem. Rev. 1999, 99 (5), 1387.
    • (1999) Chem. Rev. , vol.99 , Issue.5
  • 2
    • 0000152317 scopus 로고    scopus 로고
    • For reviews on this topic, see the special issue: Chem. Rev. 1999, 99 (5): (a) Kaselji, M.; Chung, W.-S.; le Noble, W. J. Chem. Rev. 1999, 99 (5), 1387.
    • (1999) Chem. Rev. , vol.99 , Issue.5 , pp. 1387
    • Kaselji, M.1    Chung, W.-S.2    Le Noble, W.J.3
  • 8
    • 0029968191 scopus 로고    scopus 로고
    • Carbocations which are not highly stabilized are known to be quenched by nucleophiles at the diffusional rate. See: (a) McCelland, R. A. Tetrahedron 1996, 52, 6823.
    • (1996) Tetrahedron , vol.52 , pp. 6823
    • McCelland, R.A.1
  • 12
    • 0001636598 scopus 로고
    • and references therein
    • The situation is somewhat akin to the mesomeric-field effect in aromatic systems. See: (a) Dewar, M. J. S.; Golden, R.; Harris, J. M. J. Am. Chem. Soc. 1971, 93, 4187 and references therein,
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 4187
    • Dewar, M.J.S.1    Golden, R.2    Harris, J.M.3
  • 18
    • 4043182166 scopus 로고    scopus 로고
    • note
    • 3-Sn) in solution is prevented by the marked propensity of the tin species to undergo fragmentation and, as well, its fragility under strong acidic or electrophilic conditions (refs 1b and 2).
  • 30
    • 4043125570 scopus 로고    scopus 로고
    • note
    • x.
  • 38
    • 4043166468 scopus 로고    scopus 로고
    • note
    • XSt equilibrium (dielectric constant effect).
  • 39
    • 0001376012 scopus 로고    scopus 로고
    • and references therein
    • Cieplak, A. S. Chem. Rev. 1999, 99, 1265 and references therein.
    • (1999) Chem. Rev. , vol.99 , pp. 1265
    • Cieplak, A.S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.