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Volumn 61, Issue 8, 1996, Pages 2753-2762

Reactions of charged substrates. 4. The gas-phase dissociation of (4-substituted benzyl) dimethylsulfoniums and -pyridiniums

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EID: 0001192863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951257w     Document Type: Article
Times cited : (13)

References (59)
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    • Submitted. Some results have been presented in ref 5
    • Buckley, N.; Oppenheimer, N. J. Submitted. Some results have been presented in ref 5.
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    • For reactions of 1a,c: Sneen, R. A.; Felt, G. R.; Dickason. W. C. J. Am. Chem. Soc. 1973, 95, 638-639. For the ion-pair mechanism for neutral substrates: Sneen, R. A. Acc. Chem. Res. 1973, 6, 46-53.
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  • 9
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    • note
    • That the (4-nitrobenzyl)pyridiniums also undergo homolytic cleavage is not suprising, because of all possible carbenium ions that can be produced, only the (4-nitrobenzyl)carbenium will not be stabilized by resonance, while the 4-nitrobenzyl radical would be.
  • 31
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    • and references cited therein for the work of the Cambridge group
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    • note
    • obsd.
  • 36
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    • Reference 48 has an extensive review of studies on the substitution reactions of benzyl derivatives
    • See, for example: Fujio, M.; Goto, M.; Susuki, T.; Akasaka, I.; Mishima, M.; Tsuno, Y. Bull. Chem. Soc. Jpn. 1990, 63, 1146-1153. Reference 48 has an extensive review of studies on the substitution reactions of benzyl derivatives.
    • (1990) Bull. Chem. Soc. Jpn. , vol.63 , pp. 1146-1153
    • Fujio, M.1    Goto, M.2    Susuki, T.3    Akasaka, I.4    Mishima, M.5    Tsuno, Y.6
  • 38
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    • A Simple Explanation for Curved Hammett Plots for Nucleophilic Substitution Reactions at Ring-Substituted Benzyl Derivatives
    • Chicago, IL, 22-27 Aug
    • Richard, J. P.; Yeary, P. E. A Simple Explanation for Curved Hammett Plots for Nucleophilic Substitution Reactions at Ring-Substituted Benzyl Derivatives; presented at the 206th ACS National Meeting, Chicago, IL, 22-27 Aug, 1993.
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    • note
    • 3 are much lower than those for 1a, which shows that the Hammett plot is not V-shaped as found for the benzylpyridiniums. Buckley, N. Unpublished results.
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