메뉴 건너뛰기




Volumn 2, Issue 8, 1996, Pages 1031-1040

The aminium salt and photoinduced electron transfer initiated Diels-Alder cycloaddition of electron-rich allenes: Evidence for a stepwise mechanism and the importance of steric and electronic effects for the reactivity of distonic radical cation intermediates

Author keywords

Allenes; Cycloadditions; Diels Alder reactions; Mechanistic studies; Radical cations

Indexed keywords

ALLENES; CYCLOADDITIONS; DIELS-ALDER REACTION; MECHANISTIC STUDIES; RADICAL CATIONS;

EID: 0001393337     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020820     Document Type: Article
Times cited : (25)

References (55)
  • 1
    • 84988097464 scopus 로고
    • Radical-Cation-Catalyzed Reactions, Part 7
    • Radical-Cation-Catalyzed Reactions, Part 7: M. Schmittel, H. von Seggern, Liebigs Ann. 1995, 1815-1821.
    • (1995) Liebigs Ann. , pp. 1815-1821
    • Schmittel, M.1    Von Seggern, H.2
  • 27
    • 84890847559 scopus 로고    scopus 로고
    • note
    • Unfortunately, allene 1i exhibited a strong tendency to decompose even at low temperatures, precluding its use as a radical cation.
  • 28
    • 84890847708 scopus 로고    scopus 로고
    • note
    • 1/2 = + 0.39 V vs. SCE according to our measurements (in acetonitrile).
  • 29
    • 84890818103 scopus 로고    scopus 로고
    • note
    • The preparation of norbornenes 3, 4a-c,n,o has been described in ref. [12b].
  • 31
    • 84890851297 scopus 로고    scopus 로고
    • note
    • It has previously been stated that electron-rich allenes 1a-c and diene 2 cannot react in a purely thermal or Lewis-acid-induced cycloaddition; see ref. [12].
  • 33
    • 0004186505 scopus 로고
    • red*(ET 3) = 1.58 V; see (Eds.: M. Chanon, M.-A. Fox), Elsevier, Amsterdam, Ch. 1.11
    • red*(ET 3) = 1.58 V; see M. Chanon, L. Eberson in Photoinduced Electron Transfer, Part A (Eds.: M. Chanon, M.-A. Fox), Elsevier, Amsterdam, 1988, Ch. 1.11;
    • (1988) Photoinduced Electron Transfer, Part A
    • Chanon, M.1    Eberson, L.2
  • 37
    • 0000277893 scopus 로고
    • •+, which can rather efficiently escape the solvent cage to act as a one-electron oxidant in homogeneous solution: see
    • •+, which can rather efficiently escape the solvent cage to act as a one-electron oxidant in homogeneous solution: see F. D. Lewis, R. E. Dykstra, I. R. Gould, S. Farid, J. Phys. Chem. 1988, 92, 7042-7043.
    • (1988) J. Phys. Chem. , vol.92 , pp. 7042-7043
    • Lewis, F.D.1    Dykstra, R.E.2    Gould, I.R.3    Farid, S.4
  • 41
    • 84890852579 scopus 로고    scopus 로고
    • note
    • ‡ is most likely not a minimum structure on the energy hypersurface of the radical cation cycloaddition, but rather a transition state; see ref. [26].
  • 43
    • 84890824073 scopus 로고    scopus 로고
    • note
    • • respectively. For the following discussion we assume similar solvation energies for both cations.
  • 45
    • 0027538424 scopus 로고
    • •+ should be a rather fast reaction; cf.
    • •+ should be a rather fast reaction; cf. M. Newcomb, Tetrahedron 1993, 49, 1151-1176.
    • (1993) Tetrahedron , vol.49 , pp. 1151-1176
    • Newcomb, M.1
  • 48
    • 84890812632 scopus 로고    scopus 로고
    • note
    • 1/2 (ET 5) = -0.99 V, see ref. [19c].
  • 49
    • 33751499838 scopus 로고
    • Even the p-methoxybenzyl radical is only reducible at -2.18 V vs. Fc
    • Even the p-methoxybenzyl radical is only reducible at -2.18 V vs. Fc; D. D. M. Wayner, B. A. Sim, J. J. Dannenberg, 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
  • 51
    • 84890834923 scopus 로고    scopus 로고
    • note
    • •+, that have to be optimized.
  • 54
    • 84890842739 scopus 로고    scopus 로고
    • note
    • R = 46.99 min, 54.21 min, baseline separation, endo/exo nearly 1/1).
  • 55
    • 84862394453 scopus 로고
    • Deutscher Verlag der Wissenschaften, Berlin, 18th ed.
    • Organikum, Deutscher Verlag der Wissenschaften, Berlin, 18th ed., 1990.
    • (1990) Organikum


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.