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Volumn 15, Issue 41, 2009, Pages 10713-10717

Novel oxygenations with IBX

Author keywords

Alcohols; Hydroxylation; Hypervalent compounds; Iodine; Iodoxybenzoic acid; Oxidation

Indexed keywords

2-IODOXYBENZOIC ACID; CARBONYL COMPOUNDS; HYPERVALENT COMPOUNDS; IODOXYBENZOIC ACID; KETO ESTER; OXIDIZING AGENTS;

EID: 70350231577     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901867     Document Type: Article
Times cited : (61)

References (115)
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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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    • Reference [6b]
    • 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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    • For reactions in other solvents at elevated temperatures, see: a reference [3c]; tetrafluoro-IBX is highly soluble and reactive
    • 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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    • 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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    • hydroxy ketones are also accessible by ketohydroxylation of alkenes or selective oxidation of diols-for a review, see
    • X. Baucherel, E. Levoirier, J. Uziel, S. Juge Tetrahedron Lett. 2000, 41, 1385; hydroxy ketones are also accessible by ketohydroxylation of alkenes or selective oxidation of diols-for a review, see:
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    • Baucherel, X.1    Levoirier, E.2    Uziel, J.3    Juge, S.4
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    • and references therein.
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    • iodosobenzoic acid
    • 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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    • 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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    • note
    • 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.
    • 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
    • Ozanne, A.1    Pouységu, L.2    Depernet, D.3    François, B.4    Quideau, S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.