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Volumn , Issue 7, 1997, Pages 1391-1399

Thermal and electron-transfer induced reactions of enediynes and enyne-allenes, 9: Electron-transfer versus acid catalysis in enediyne cyclizations

Author keywords

Cyclic voltammetry; Cyclization; Electron transfer; Enediyne; Radical cations

Indexed keywords


EID: 33748810520     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970716     Document Type: Article
Times cited : (13)

References (57)
  • 31
    • 33748840703 scopus 로고    scopus 로고
    • All potentials are referenced to the ferrocene/ferrocenium (Fc) couple unless otherwise noted. To obtain values vs. SCE simply add +0.39 V
    • All potentials are referenced to the ferrocene/ferrocenium (Fc) couple unless otherwise noted. To obtain values vs. SCE simply add +0.39 V.
  • 33
    • 33748838201 scopus 로고    scopus 로고
    • [6]
    • [6].
  • 35
    • 0000628641 scopus 로고
    • A detailed and critical evaluation of the use of thermochemical cycles has been given by Wayner and Parker: D. M. M. Wayner, V. D. Parker, Acc. Chem. Res. 1993, 26, 287-294.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 287-294
    • Wayner, D.M.M.1    Parker, V.D.2
  • 48
    • 33748828046 scopus 로고    scopus 로고
    • On the other hand, enediynes 3 showed no analogous acid-induced cyclization, which may be rationalized by the different protonation behavior of 1 and 3. Since enediynes 1a and b are protonated at the acetylenic carbon atom C-2 to preserve aromaticity of all 3 aryl groups, a cationic cyclization onto the second triple bond can easily take place. In contrast, in enediynes 3 protonation occurs reversibly at the central double bond which does not lead to intramolecular cyclizations
    • On the other hand, enediynes 3 showed no analogous acid-induced cyclization, which may be rationalized by the different protonation behavior of 1 and 3. Since enediynes 1a and b are protonated at the acetylenic carbon atom C-2 to preserve aromaticity of all 3 aryl groups, a cationic cyclization onto the second triple bond can easily take place. In contrast, in enediynes 3 protonation occurs reversibly at the central double bond which does not lead to intramolecular cyclizations.
  • 53
    • 33748836296 scopus 로고    scopus 로고
    • -1)
    • -1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.