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Page, P.C.B.1
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oxidative deprotection of dithianes
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70350251333
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see reference [5c]; aromatization of dihydropyridines
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f) see reference [5c]; aromatization of dihydropyridines:
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41
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34547403674
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oxidative cyclizalion of anilides
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Angew. Chem. Int. Ed. 2007, 46, 5775; oxidative cyclizalion of anilides:
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Angew. Chem. Int. Ed.
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generation of radicals
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rearrangement of thioketals
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51
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70350254831
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Details of this hitherto unknown direct transformation of 2-oxonilriles into their unsaturated counterparts will be discussed in an upcoming publication.
-
Details of this hitherto unknown direct transformation of 2-oxonilriles into their unsaturated counterparts will be discussed in an upcoming publication.
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a) Reference [6b];
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60
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a Reference [6b]
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The viability of alkynyl substituents Z in 1BX-mediated oxygenations was found to be limited due to facile double bond isomerizalion to the corresponding alienes.
-
The viability of alkynyl substituents Z in 1BX-mediated oxygenations was found to be limited due to facile double bond isomerizalion to the corresponding alienes.
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70
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70350250109
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For reactions in other solvents at elevated temperatures, see: a reference [3c]; tetrafluoro-IBX is highly soluble and reactive
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For reactions in other solvents at elevated temperatures, see: a) reference [3c]; tetrafluoro-IBX is highly soluble and reactive:
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Concurrently. IBX was slowly reduced to IBA by DMSO: see also: Reference [6b].
-
Concurrently. IBX was slowly reduced to IBA by DMSO: see also: Reference [6b].
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74
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selective oxidations of sulfides to sulfoxides
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Synthesis and structure: a) V. V. Zhdankin, D. N. Litvinov, A. Y. Koposov, T. Luu, M. J. Ferguson, R. McDonald, R. R. Tykwinski. Chem. Commun. 2004, 106; selective oxidations of sulfides to sulfoxides:
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Alternative strategies for the direct a-hydroxylation of carbonyl. compounds are available; for reviews, see: a) J. Christoffers, A. Baro, T. Werner, Adv. Synth. Catal. 2004, 346, 143;
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iodosobenzoic acid
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The a-oxygenation of carbonyl compounds (not the synthesis of tertiary alcohols) has also been accomplished using other hypervalent iodine reagents. Iodosobenzene: a) R. M. Moriarty, S. C Gupta, H. Hu, D. R. Berenschot, K. B. White, J. Am. Chem. Soc. 1981, 103, 686; iodosobenzoic acid:
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catalytic a-oxygenation
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Altermann, S.M.1
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70350251328
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For example, Rubottom oxidation of the corresponding silyl enol ether afforded 7g in a yield of only 7% according to reference [19a].
-
For example, Rubottom oxidation of the corresponding silyl enol ether afforded 7g in a yield of only 7% according to reference [19a].
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106
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70350245966
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note
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The conversion of thioamides into the corresponding carbonyl compounds appears to be a general reaction. This process occurs more rapidly than the subsequent hydroxylation: Figure presented
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Prof. Dr. Quideau is gratefully acknowledged for providing a generous sample of SIBX.
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The reaction 6->7 also proceeds when the stabilized formulation SIBX is employed as the oxidizing agent (A. Ozanne, L. Pouységu, D. Depernet, B. François, S. Quideau, Org. Lett. 2003, 5, 2903); Prof. Dr. Quideau is gratefully acknowledged for providing a generous sample of SIBX.
-
(2003)
Org. Lett.
, vol.5
, pp. 2903
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Ozanne, A.1
Pouységu, L.2
Depernet, D.3
François, B.4
Quideau, S.5
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115
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0030004526
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A.-M. Lluch, M. Gibert, F. Sánchez-Baeza, A. Messeguer, Tetrahedron 1996, 52, 3973.
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(1996)
Tetrahedron
, vol.52
, pp. 3973
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Lluch, A.-M.1
Gibert, M.2
Sánchez-Baeza, F.3
Messeguer, A.4
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