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Volumn 118, Issue 46, 1996, Pages 11434-11445

Mechanism for nucleophilic substitution and elimination reactions at tertiary carbon in largely aqueous solutions: Lifetime of a simple tertiary carbocation

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLBENZENE;

EID: 0029982116     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9617451     Document Type: Article
Times cited : (80)

References (91)
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    • + of these reactions.
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    • note
    • 2O, which contains 42 wt % water.
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    • 0000782883 scopus 로고
    • obsd for reaction of H-5 and MeO-5 is consistent with only a small inductive effect of the 4-MeO substituent on the reaction, and it shows that there is no significant movement of positive charge from the developing carbocation onto the aromatic ring [Brown, H. C.; Kim, C. J. J. Am. Chem. Soc. 1968, 90, 2082-2096].
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    • + which was determined in this work.
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    • note
    • -1).
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    • note
    • s= 13.1.
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    • 1-Br is too reactive to accumulate during the reaction of 1-Cl in the presence of NaBr because febsd values for reaction of tert-butyl bromide in mixed aqueous/organic solvents are ca, 40-fold larger than those for reaction of tert-butyl chloride under the same conditions [Harris, J. M.; Mount, D. L.; Smith, M. R.; Neal, W. C., Jr.; Dukes, M. D.; Raber, D. J. J. Am. Chem. Soc. 1978, 100, 8147-8155].
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    • note
    • - within this complex is much greater than that of the surrounding solvent molecules.
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    • The most careful correlation of these data is consistent with the conclusion that there is a small amount of nucleophilic assistance to the ionization of tert-butyl derivatives [Bentley, T. W.; Roberts, K. J. Chem. Soc., Perkin Trans. 2 1989, 1055-1060].
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.