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For a general review of allylic oxidation see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 7, p 83.
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Bulman Page, P.C.1
McCarthy, T.J.2
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2
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0037205912
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For asymmetric allylic oxidations see: (a) Andrus, M. B.; Zhou, Z. J. Am. Chum. Soc. 2002, 124, 8806. (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
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Andrus, M.B.1
Zhou, Z.2
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3
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0037185537
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For asymmetric allylic oxidations see: (a) Andrus, M. B.; Zhou, Z. J. Am. Chum. Soc. 2002, 124, 8806. (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
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Andrus, M.B.1
Lashley, J.C.2
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4
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0035476406
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For asymmetric allylic oxidations see: (a) Andrus, M. B.; Zhou, Z. J. Am. Chum. Soc. 2002, 124, 8806. (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
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Eames, J.1
Watkinson, M.2
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5
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0037454309
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Recent work: (a) Yu, J.-Q.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 3232. (b) Yu, J.-Q.; Corey, E. J. Org. Lett. 2002, 4, 2727. (c) Crich, D.; Zou, Y. Org. Lett. 2004, 6, 775.
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Yu, J.-Q.1
Corey, E.J.2
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Yu, J.-Q.1
Corey, E.J.2
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7
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Recent work: (a) Yu, J.-Q.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 3232. (b) Yu, J.-Q.; Corey, E. J. Org. Lett. 2002, 4, 2727. (c) Crich, D.; Zou, Y. Org. Lett. 2004, 6, 775.
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Crich, D.1
Zou, Y.2
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Sharpless, K.B.1
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Academic Press: New York
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Selected reviews: (a) Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12, 63. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981. (c) Metal-Catalyzed Selective Oxidations. In Peroxide Chemistry Mechanistic and Preparative Aspects of Oxygen Transfer; Adam, W., Ed.; Wiley: Weinheim, 2000; p 301.
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Sheldon, R.A.1
Kochi, J.K.2
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6444220517
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Metal-Catalyzed Selective Oxidations
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Selected reviews: (a) Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12, 63. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981. (c) Metal-Catalyzed Selective Oxidations. In Peroxide Chemistry Mechanistic and Preparative Aspects of Oxygen Transfer; Adam, W., Ed.; Wiley: Weinheim, 2000; p 301.
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(b) Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Organomet. Chem. 1979, 166, 79.
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Noels, A.F.1
Hubert, A.J.2
Teyssie, P.3
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4 catalyzes the quantitative decomposition of TBHP: Doyle, M. P.; Terpstra, J. W.; Winter, C. H.; Griffin, J. H. J. Mol. Catal. 1984, 26, 259.
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(a) Das, K.; Kadish, K. M.; Bear, J. L. Inorg. Chem. 1978, 17, 930.
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(b) Zhu, T. P.; Ahsan, M. Q.; Malinski, T.; Kadish, K. M.; Bear, J. L. Inorg. Chem. 1984, 23, 2.
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Zhu, T.P.1
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Bear, J.L.5
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23
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6444235247
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-
note
-
Enedione 2 is a nonvolatile solid allowing rapid purification and determination of yield.
-
-
-
-
24
-
-
6444237339
-
-
note
-
Anhydrous tert-butyl hydroperoxide in decane was obtained from Aldrich.
-
-
-
-
25
-
-
6444241955
-
-
note
-
Longer reaction times did not increase yield.
-
-
-
-
26
-
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6444243339
-
-
note
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For tert-butyl peroxy ethers as intermediates, see: refs 3a, 3b, and 6c.
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-
-
-
28
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-
6444231454
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See Supporting Information for optimization results
-
See Supporting Information for optimization results.
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-
-
-
29
-
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6444233226
-
-
note
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2) yielded the analytically pure compound.
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-
-
-
30
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0001135955
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(a) Kinzer, G. W.; Fentiman, A. F., Jr.; Foltz, R. L.; Rudinskyy, J. A. J. Econ. Entomol. 1971, 64, 970.
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-
Kinzer, G.W.1
Fentiman Jr., A.F.2
Foltz, R.L.3
Rudinskyy, J.A.4
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31
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6444221892
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-
See Supporting Information for UV-visible spectrum
-
See Supporting Information for UV-visible spectrum.
-
-
-
-
34
-
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6444236687
-
-
note
-
5+ complex. Efforts are underway to obtain a crystal structure of this complex.
-
-
-
-
37
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0001605611
-
-
and references therein
-
Bravo, A.; Bjorsvik, H.-R.; Fontana, F.; Liguori, L.; Minisci, F. J. Org. Chem. 1997, 62, 3849 and references therein.
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Bravo, A.1
Bjorsvik, H.-R.2
Fontana, F.3
Liguori, L.4
Minisci, F.5
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41
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37049083063
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(d) Araneo, S.; Fontana, F.; Minisci, F.; Recupero, F.; Serri, A. J. Chem. Soc., Chem. Commun. 1995, 1399.
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Araneo, S.1
Fontana, F.2
Minisci, F.3
Recupero, F.4
Serri, A.5
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42
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0000887096
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(e) Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F.; Banfi, S.; Quid, S. J. Am. Chem. Soc. 1995, 117, 226.
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Minisci, F.1
Fontana, F.2
Araneo, S.3
Recupero, F.4
Banfi, S.5
Quid, S.6
-
43
-
-
6444223436
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-
note
-
We have isolated 7 (where R = Ph) from the oxidation of 1-phenylcyclohexene. Resubmitting 7 to the reaction resulted in quantitative conversion to the product shown in Table I, entry 3. See Supporting Information for details.
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