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(Ed.: D. Klamann), Thieme, Stuttgart, New York
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For accounts on sulfoxide synthesis and application see: a) K.-D. Gundermann, K. Hümke, Methoden Org. Chem. (Houben-Weyl) Organische Schwefel-Verbindungen, Vol. E11/Teil 1 (Ed.: D. Klamann), Thieme, Stuttgart, New York, 1985;
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0003491250
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b) T. Durst in Comprehensive Organic Chemistry, Vol. 5 (Ed.: D. N. Jones), Pergamon, Oxford, 1979, Sections 11.6 and 11.7;
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Durst, T.1
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(Ed.: B. M. Trost), Pergamon, Oxford, Section 1.5
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c) G. Solladie in Comprehensive Organic Synthesis, Vol. 6 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, Section 1.5;
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Solladie, G.1
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(Ed.: B. M. Trost), Pergamon, Oxford, Section 6.2.
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d) S. Uemura in Comprehensive Organic Synthesis, Vol. 6 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, Section 6.2.
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Uemura, S.1
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0006508763
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For some examples where extreme or less economical conditions seem necessary see: a) S. Vayssié, H. Elias, Angew. Chem. 1998, 110, 2246; Angew. Chem. Int. Ed. 1998, 37, 2088 (use of in situ nitrous acid);
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Vayssié, S.1
Elias, H.2
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0032541273
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use of in situ nitrous acid
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For some examples where extreme or less economical conditions seem necessary see: a) S. Vayssié, H. Elias, Angew. Chem. 1998, 110, 2246; Angew. Chem. Int. Ed. 1998, 37, 2088 (use of in situ nitrous acid);
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Angew. Chem. Int. Ed.
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19
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0343035615
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μ-oxo diferric complexes
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c) C. Duboc-Toia, S. Menage, C. Lambeaux, M. Fontecave, Tetrahedron Lett. 1987, 38, 3727 (μ-oxo diferric complexes);
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Duboc-Toia, C.1
Menage, S.2
Lambeaux, C.3
Fontecave, M.4
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20
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0032581561
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methyltrioxorhenium (MTO) plus urea hydrogen peroxide
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d) H. Q. N. Gunaratne, M. A. McKervey, S. Feutren, J. Finlay, J. Boyd, Tetrahedron Lett. 1998, 39, 5655 (methyltrioxorhenium (MTO) plus urea hydrogen peroxide);
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Gunaratne, H.Q.N.1
McKervey, M.A.2
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23
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84981440745
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S. Ghisla, U. Hartmann, P. Hemmerich, F. Müller, Liebigs Ann. Chem. 1973, 1388.
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Liebigs Ann. Chem.
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Ghisla, S.1
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Müller, F.4
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24
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85007632107
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note
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The excess was mainly used to obtain better accuracy in the determination of the initial rate of the noncatalyzed reaction.
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25
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85007653134
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note
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Furthermore, simple alkenes such as styrene did not oxidize under the reaction conditions.
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26
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0033591184
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H. Adolfsson, A. Converso, K. B. Sharpless, Tetrahedron Lett. 1999, 40, 3991. An exception is the MTO/urea hydrogen peroxide system, which is compatible with alkenes, see ref. [7d].
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Tetrahedron Lett.
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Adolfsson, H.1
Converso, A.2
Sharpless, K.B.3
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27
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85007628816
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note
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Only partial decomposition of starting material (2-(phenylthio)-1,4-benzoquinone) could be detected by NMR.
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28
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37049079312
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See for esample V. K. Aggarwal, I. W. Davies, R. Franklin, J. Maddock, M. F. Mahon, K. C. Molloy, J. Chem. Soc. Perkin Trans. 1 1994, 2363.
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Aggarwal, V.K.1
Davies, I.W.2
Franklin, R.3
Maddock, J.4
Mahon, M.F.5
Molloy, K.C.6
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30
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0017784006
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2, see ref. [1e] and C. Kemal, T. W. Chan, T. C. Bruice, J. Am. Chem. Soc. 1977, 99, 7272.
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Kemal, C.1
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31
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85007628843
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note
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The oxidation of thioethers can be looked upon as a borderline case, since for example the equilibrium between I, IV, and III can play a greater role depending on experimental conditions.
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32
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85007643612
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note
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An alternative activation mechanism, even though less likely, where hydrogen peroxide electrophilically (!) attacks the flavin, can not be ruled out.
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33
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85007646622
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note
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Murahashi and co-workers have previously discussed such possible equilibria, see ref. [2].
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34
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85007643613
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note
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Murahashi used the perchlorate analogue of IVb as catalyst precursor.
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37
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85007646620
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note
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Fro example, the solubility and yields are rather low for most precursors substituted at positions 7, 8, and/or 10.
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38
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84889582115
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H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 1997, 62, 7512.
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Gottlieb, H.E.1
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Nudelman, A.3
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40
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85007625392
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note
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The exact value was not determinable, since the melting point exceeded the max. temperature of the apparatus.
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41
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85007643104
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note
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13C NMR spectrum.
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42
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85007643102
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note
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When using less catalyst/peroxide the reactions were followed up to 360 min with 30-60 min intervals after the first hour.
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44
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85007626314
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note
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When using less catalyst/peroxide the reactions were followed up to 360 min with 30-60 min intervals after the first hour.
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47
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0001157785
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E. Juaristi, J. Guzmán, V. V. Kane, R. S. Glass, Tetrahedon 1984, 40, 1477.
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Tetrahedon
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Juaristi, E.1
Guzmán, J.2
Kane, V.V.3
Glass, R.S.4
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