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Volumn 69, Issue 2, 2004, Pages 482-486

Spectroscopic Detection, Reactivity, and Acid-Base Behavior of Ring-Dimethoxylated Phenylethanoic Acid Radical Cations and Radical Zwitterions in Aqueous Solution

Author keywords

[No Author keywords available]

Indexed keywords

OXIDATION; PH EFFECTS; POSITIVE IONS; RATE CONSTANTS;

EID: 0345871939     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035492n     Document Type: Article
Times cited : (12)

References (39)
  • 15
    • 0345928787 scopus 로고    scopus 로고
    • note
    • The following one-electron oxidation potentials have been determined in aqueous solution for anisole, 1,2-, 1,3-, and 1,4-dimethoxybenzene respectively 1.62, 1.44, 1.58, and 1.30 V/NHE,10 substrates which can be taken as models for 1, 3 (and 4), 5, and 6, respectively.
  • 25
    • 33751499838 scopus 로고
    • No direct evidence for the formation of the ring-dimethoxylated benzyl radicals was obtained. It is, however, possible that under oxidative conditions, due to their very low oxidation potential, these radicals are rapidly oxidized to the corresponding cations. See for example: Wayner, D. D. M.; Sim, B. A.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 4853-4858.
    • (1991) J. Org. Chem. , vol.56 , pp. 4853-4858
    • Wayner, D.D.M.1    Sim, B.A.2    Dannenberg, J.J.3
  • 28
    • 0347189906 scopus 로고    scopus 로고
    • note
    • This notation represents an oversimplification since, as compared to the radical cations, the corresponding radical zwitterions lack the presence of the carboxylic proton.
  • 38
    • 0347820140 scopus 로고    scopus 로고
    • note
    • In light of this observation, in the mechanism shown in Scheme 2 the possibility that decarboxylation is concerted with electron removal from the aromatic ring, bypassing 4-methoxyphenylacetoxyl radical formation, should also be considered.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.