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(f) Wagner, P. J. In Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M.; Lenci, F., Eds.; CRC Press: Boca Raton, 2003, Chap. 58.
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For recent reviews, see: a, Renaud, P, Sibi, M. P, Eds, Wiley-VCH: Weinheim
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For recent reviews, see: (a) Wessig, P. In Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001, 523.
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For discussions of the lifetime of diradicals in solution, see: a, and references cited therein
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For discussions of the lifetime of diradicals in solution, see: (a) Johnston, L. J.; Scaiano, J. C. Chem. Rev. 1989, 89, 521; and references cited therein.
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Majima, T.7
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(a) Dupuis, J.; Giese, B.; Rüegge, D.; Fischer, H.; Korth, H.-G.; Sustman, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 896.
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and references therein
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(a) Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70.
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Chem. Int. Ed, and references therein
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(c) Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem. Int. Ed. 1999, 38, 2586; and references therein.
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Giese, B.1
Wettstein, P.2
Stähelin, C.3
Barbosa, F.4
Neuburger, M.5
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Wessig, P.7
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26
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0004288915
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For recent reviews, see: a, Hanessian, S, Ed, Marcel Dekker: New York
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For recent reviews, see: (a) Giese, B.; Zeitz, H.-G. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997, 507.
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(b) Pearce, A. J.; Mallet, J.-M.; Sinaÿ, P. In Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001, 523.
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Pearce, A.J.1
Mallet, J.-M.2
Sinaÿ, P.3
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28
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34547655226
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The numbering system used throughout the text is based on 1-methyl-2,3-alkanedione and corresponds to that depicted in structures of Table 1 and Schemes 1-3.
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The numbering system used throughout the text is based on 1-methyl-2,3-alkanedione and corresponds to that depicted in structures of Table 1 and Schemes 1-3.
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29
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0030457582
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The 1,2-diketones 1-4 shown in Table 1 were prepared from their corresponding alkynes via ozonolysis: (a) Favino, T. F.; Fronza, G.; Fuganti, C.; Fuganti, D.; Graselli, P.; Mele, A. J. Org. Chem. 1996, 61, 8975.
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The 1,2-diketones 1-4 shown in Table 1 were prepared from their corresponding alkynes via ozonolysis: (a) Favino, T. F.; Fronza, G.; Fuganti, C.; Fuganti, D.; Graselli, P.; Mele, A. J. Org. Chem. 1996, 61, 8975.
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84986409344
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4: Zibuck, R.; Seebach, D. Helv. Chim. Acta 1988, 71, 237.
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4: Zibuck, R.; Seebach, D. Helv. Chim. Acta 1988, 71, 237.
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34547701649
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1H NMR spectroscopic analysis.
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1H NMR spectroscopic analysis.
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33
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0009646602
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Walther, K.; Kranz, U.; Henning, H.-G. J. Prakt. Chem. 1987, 329, 859.
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Walther, K.1
Kranz, U.2
Henning, H.-G.3
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34
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A 450 W ACE-Hanovia medium-pressure mercury lamp in an immersion well with 4.8 mm Pyrex walls.
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A 450 W ACE-Hanovia medium-pressure mercury lamp in an immersion well with 4.8 mm Pyrex walls.
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35
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0001694916
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The term of 'memory of chirality' is used here with the meaning that was proposed by Fuji: Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373.
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(a) The term of 'memory of chirality' is used here with the meaning that was proposed by Fuji: Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373.
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36
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0033520303
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For a discussion on the memory effect in photochemical reactions, see:, Chem. Int. Ed, and references therein
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(b) For a discussion on the memory effect in photochemical reactions, see: Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem. Int. Ed. 1999, 38, 2586; and references therein.
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(1999)
Angew
, vol.38
, pp. 2586
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Giese, B.1
Wettstein, P.2
Stähelin, C.3
Barbosa, F.4
Neuburger, M.5
Zehnder, M.6
Wessig, P.7
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37
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34547656985
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3, UV lamp (10 cm).
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3, UV lamp (10 cm).
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38
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18244373174
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To see a list of procedures to generate C-ketosides: Roberts, S. W.; Rainier, J. D. Org. Lett. 2005, 7, 1141.
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To see a list of procedures to generate C-ketosides: Roberts, S. W.; Rainier, J. D. Org. Lett. 2005, 7, 1141.
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39
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34547652056
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General Procedure for the Photocyclization of 1,2-Diketones The corresponding 1,2-diketone placed in a Pyrex vessel with or without the indicated solvent (approx. 0.05 M) was irradiated with sunlight or a UV lamp, placed at 10 cm distance from the flask, until the reaction turned colorless. If it proceeded, the mixture was concentrated in vacuo. Column or Chromatotron® chromatography of the residue (hexanes-EtOAc mixtures) afforded the cyclic compounds. General Procedure for the Photocyclization of 1,2-Diketones with Photosensitizers The corresponding 1,2-diketone (0.038 mmol) and photosensitizer (benzophenone or pyrene; 0.5 mmol) was dissolved in CDCl3 (1 mL) and placed in a NMR tube. The reaction mixture was irradiated with an UV lamp, placed at 10 cm distance from the flask, until complete conversion and the solvent was removed under vacuum. The reaction was monitored by 1H NMR. Chromatotron® chromatography of the residue with hexanes to r
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3): δ = 1.37 (3 H, s), 2.62 (1 H, d, J = 17.5 Hz), 3.31 (1 H, d, J = 17.5 Hz), 3.50 (1 H, m), 3.55 (1 H, m), 3.60 (1 H, t, J = 8.8 Hz), 3.70 (1 H, d, J = 8.6 Hz), 3.61-3.79 (2 H, m), 4.44 (1 H, d, J = 11.7 Hz), 4.46 (1 H, d, J = 11.8 Hz), 4.53 (1 H, d, J = 10.8 Hz), ...
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