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Volumn 132, Issue 31, 2010, Pages 10662-10664

1,4,7-trimethyloxatriquinane: SN2 reaction at tertiary carbon

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL MODELING; ELEVATED TEMPERATURE; MECHANISTIC INTERPRETATIONS; OXONIUM; SALT EFFECT;

EID: 77955373368     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103880c     Document Type: Article
Times cited : (38)

References (14)
  • 6
    • 84914260997 scopus 로고
    • For related studies in DMF solvent, see
    • For related studies in DMF solvent, see: Cook, D. and Parker, A. J. J. Chem. Soc. B 1968, 142
    • (1968) J. Chem. Soc. B , pp. 142
    • Cook, D.1    Parker, A.J.2
  • 10
    • 77955402355 scopus 로고    scopus 로고
    • Calculations were performed using the density functional B3LYP method with the 6-31G(d,p) basis set. Optimizations were done both in the gas phase and in a polarizable continuum solvent model (methanol, E = 32.63) using the CPCM method with United Atom Topological Model radii. Default optimization parameters in the Gaussian03 program were applied
    • Calculations were performed using the density functional B3LYP method with the 6-31G(d,p) basis set. Optimizations were done both in the gas phase and in a polarizable continuum solvent model (methanol, E = 32.63) using the CPCM method with United Atom Topological Model radii. Default optimization parameters in the Gaussian03 program were applied
  • 11
    • 0038626673 scopus 로고    scopus 로고
    • revision D.01; Gaussian, Inc.: Wallingford, CT.
    • Frisch, M. J. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 14
    • 77955403766 scopus 로고
    • We note that 1 is not the only example of a tertiary oxonium ion. Gargiulo and Tarbell in 1969 described 1,2,2,5-tetramethyltetrahydrofuran, which was stable enough to be isolated. It did, however, show reactivity that would be expected of a 3° oxonium salt, solvolyzing with ethanol by exclusive attack at the 2-position
    • We note that 1 is not the only example of a tertiary oxonium ion. Gargiulo and Tarbell in 1969 described 1,2,2,5-tetramethyltetrahydrofuran, which was stable enough to be isolated. It did, however, show reactivity that would be expected of a 3° oxonium salt, solvolyzing with ethanol by exclusive attack at the 2-position: Gargiulo, R. J. and Tarbell, D. S. Proc. Natl. Acad. Sci. U.S.A. 1969, 62, 52
    • (1969) Proc. Natl. Acad. Sci. U.S.A. , vol.62 , pp. 52
    • Gargiulo, R.J.1    Tarbell, D.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.