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Volumn 68, Issue 13, 2003, Pages 5399-5402

Solvolysis of (Z)-5-trimethylstannyl 2-adamantyl p-bromobenzenesulfonate: Mechanistic implications of a record-breaking secondary α-deuterium kinetic isotope effect for an SN1 substrate

Author keywords

[No Author keywords available]

Indexed keywords

ISOTOPES; SUBSTRATES; TIN COMPOUNDS;

EID: 0037870781     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0300892     Document Type: Article
Times cited : (17)

References (41)
  • 6
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    • and references therein
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  • 11
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    • note
    • (a) For a summary of references concerning the use of the secondary α-deuterium isotopic effect (α-kie) as a mechanistic probe and, in particular, for characterizing solvolytic reactions of secondary alkyl arenesulfonates, see refs 8b and c.
  • 14
    • 0037978790 scopus 로고    scopus 로고
    • note
    • N1 substrate that reacts with rate-limiting ionization with no internal return. Recent results confirm that it ionizes without methyl participation in the rate-determining step and that methyl migration occurs rapidly after formation of the secondary tight ion pair.
  • 16
    • 0038316225 scopus 로고    scopus 로고
    • note
    • 3; 70E)
  • 17
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    • note
    • (b) Taken from ref 10d.
  • 18
    • 0037978783 scopus 로고    scopus 로고
    • note
    • (c) Oxygen-18 scrambling studies were performed according to the procedure outlined in ref 8c.
  • 19
    • 0037640765 scopus 로고
    • Ph.D. Dissertation, Indiana University, Bloomington, Indiana
    • (d) Coope, J. Ph.D. Dissertation, Indiana University, Bloomington, Indiana, 1990.
    • (1990)
    • Coope, J.1
  • 21
    • 0037640764 scopus 로고    scopus 로고
    • note
    • (a) Possibility of a steric factor being responsible for less internal return in the case of solvolysis of the (Z)-isomer has been previously canvassed.
  • 25
    • 0006073669 scopus 로고
    • Wadt, W. R.; Hay, P.J. J. Chem. Phys. 1985, 82, 284. Hay, P. J.; Wadt, W. R J. Chem. Phys. 1985, 82, 270. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
    • (1985) J. Chem. Phys. , vol.82 , pp. 284
    • Wadt, W.R.1    Hay, P.J.2
  • 26
    • 33745770836 scopus 로고
    • Wadt, W. R.; Hay, P.J. J. Chem. Phys. 1985, 82, 284. Hay, P. J.; Wadt, W. R J. Chem. Phys. 1985, 82, 270. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
    • (1985) J. Chem. Phys. , vol.82 , pp. 270
    • Hay, P.J.1    Wadt, W.R.2
  • 27
    • 27344448074 scopus 로고
    • Wadt, W. R.; Hay, P.J. J. Chem. Phys. 1985, 82, 284. Hay, P. J.; Wadt, W. R J. Chem. Phys. 1985, 82, 270. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
    • (1985) J. Chem. Phys. , vol.82 , pp. 299
    • Hay, P.J.1    Wadt, W.R.2
  • 28
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    • Unpublished results
    • Sorensen, T. S. Unpublished results.
    • Sorensen, T.S.1
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    • note
    • imag = 0 and 1, respectively.
  • 35
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    • note
    • 3) involves the formation of the (Z)- tight ion pair, which may undergo internal return or competitively invert to the (E)- ion pair.
  • 39
    • 0038316215 scopus 로고    scopus 로고
    • note
    • (a) BIPCON instrument was a modification of the equipment utilized by Tilley and Shiner. A full description is given by Milne.
  • 41
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    • Ph.D. Thesis, University of Adelaide, Adelaide, Australia
    • Milne, I. R. Ph.D. Thesis, University of Adelaide, Adelaide, Australia, 2002.
    • (2002)
    • Milne, I.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.