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Radical-Cation-Catalyzed Reactions, Part 7
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a) M. Schmittel, C. Wöhrle, Tetrahedron Lett. 1993, 34, 52, 8431-8434;
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Schmittel, M.1
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27
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84890847559
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note
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Unfortunately, allene 1i exhibited a strong tendency to decompose even at low temperatures, precluding its use as a radical cation.
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-
-
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28
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84890847708
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note
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1/2 = + 0.39 V vs. SCE according to our measurements (in acetonitrile).
-
-
-
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29
-
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84890818103
-
-
note
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The preparation of norbornenes 3, 4a-c,n,o has been described in ref. [12b].
-
-
-
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30
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84890854448
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M. Keller, H. von Seggern, M. Schmittel, C. Wöhrle, Z. Kristallogr. 1995, 210, 602-604.
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Keller, M.1
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Wöhrle, C.4
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31
-
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84890851297
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-
note
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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].
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-
-
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33
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0004186505
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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;
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(1988)
Photoinduced Electron Transfer, Part A
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Chanon, M.1
Eberson, L.2
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34
-
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0001760282
-
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red*(ET 5) = 1.35 V; see
-
red*(ET 5) = 1.35 V; see M. Martiny, E. Steckhan, T. Esch, Chem. Ber. 1993, 126, 1671-1682.
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Chem. Ber.
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Martiny, M.1
Steckhan, E.2
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35
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0026667909
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a) G. Pandey, K. Sudha Rani, G. Lakshmaiah, Tetrahedron Lett. 1992, 33, 5107-5110;
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Pandey, G.1
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36
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84943972570
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b) E. Vauthey, P. Suppan, E. Haselbach, Helv. Chim. Acta 1988, 71, 93-99.
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Vauthey, E.1
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37
-
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0000277893
-
-
•+, 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.
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Lewis, F.D.1
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38
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0020736210
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N. L. Bauld, D. J. Bellville, R. Pabon, R. Chelsky, G. Green, J. Am. Chem. Soc. 1983, 105, 2378-2382.
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Bauld, N.L.1
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Green, G.5
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39
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0000929237
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A. Gieseler, E. Steckhan, O. Wiest, F. Knoch, J. Org. Chem. 1991, 56, 1405-1411.
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Gieseler, A.1
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40
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33749025423
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R. M. Wilson, J. G. Dietz, T. A. Shepherd, D. M. K. Ho, A. Schnapp, R. C. Elder, J. W. Watkins, II, L. S. Geraci, C. F. Campana, J. Am. Chem. Soc. 1989, 111, 1749-1754.
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Wilson, R.M.1
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Watkins II, J.W.7
Geraci, L.S.8
Campana, C.F.9
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41
-
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84890852579
-
-
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
-
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84890824073
-
-
note
-
• respectively. For the following discussion we assume similar solvation energies for both cations.
-
-
-
-
44
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0842341771
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M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
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Dewar, M.J.S.1
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Stewart, J.J.P.4
-
45
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0027538424
-
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•+ should be a rather fast reaction; cf.
-
•+ should be a rather fast reaction; cf. M. Newcomb, Tetrahedron 1993, 49, 1151-1176.
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(1993)
Tetrahedron
, vol.49
, pp. 1151-1176
-
-
Newcomb, M.1
-
48
-
-
84890812632
-
-
note
-
1/2 (ET 5) = -0.99 V, see ref. [19c].
-
-
-
-
49
-
-
33751499838
-
-
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.
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J. Org. Chem.
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Wayner, D.D.M.1
Sim, B.A.2
Dannenberg, J.J.3
-
50
-
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33845278203
-
-
1/2 = - 0.23 V vs. Fc; see
-
1/2 = - 0.23 V vs. Fc; see D. D. M. Wayner, D. J. McPhee, D. Griller, J. Am. Chem. Soc. 1988, 110, 132-137.
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(1988)
J. Am. Chem. Soc.
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Wayner, D.D.M.1
McPhee, D.J.2
Griller, D.3
-
51
-
-
84890834923
-
-
note
-
•+, that have to be optimized.
-
-
-
-
54
-
-
84890842739
-
-
note
-
R = 46.99 min, 54.21 min, baseline separation, endo/exo nearly 1/1).
-
-
-
-
55
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84862394453
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Deutscher Verlag der Wissenschaften, Berlin, 18th ed.
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Organikum, Deutscher Verlag der Wissenschaften, Berlin, 18th ed., 1990.
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(1990)
Organikum
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